An official website of the United States government

Cisplatin

PubChem CID
5460033
Structure
Cisplatin_small.png
Molecular Formula
Synonyms
  • Cisplatina
  • Citoplatino
  • Cysplatyna
  • Metaplatin
  • Plastistil
Molecular Weight
300.05 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-11
Description
Cisplatin, cisplatinum or cis-diamminedichloroplatinum(II) (CDDP) is a platinum-based chemotherapy drug used to treat various types of cancers, including sarcomas, some carcinomas (e.g. small cell lung cancer, and ovarian cancer), lymphomas and germ cell tumors. It was the first member of its class, which now also includes carboplatin and oxaliplatin.
Cisplatin is the prototype platinum coordination complex classified as an alkylating agent and used intravenously in the treatment of several forms of cancer. Cisplatin has been associated with a low rate of serum enzyme elevations and with rare cases of clinically apparent, acute liver injury.
Cisplatin is an alkylating-like inorganic platinum agent (cis-diamminedichloroplatinum) with antineoplastic activity. Cisplatin forms highly reactive, charged, platinum complexes which bind to nucleophilic groups such as GC-rich sites in DNA inducing intrastrand and interstrand DNA cross-links, as well as DNA-protein cross-links. These cross-links result in apoptosis and cell growth inhibition.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Cisplatin.png

1.2 3D Status

Conformer generation is disallowed since MMFF94s unsupported element, mixture or salt

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

azane;dichloroplatinum
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

LXZZYRPGZAFOLE-UHFFFAOYSA-L
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

N.N.Cl[Pt]Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

Cl2H6N2Pt
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 DrugBank ID

2.3.4 KEGG ID

2.3.5 NCI Thesaurus Code

2.3.6 RXCUI

2.3.7 Wikidata

2.3.8 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Biocisplatinum
  • cis Diamminedichloroplatinum
  • cis Platinum
  • cis-Diamminedichloroplatinum
  • cis-Diamminedichloroplatinum(II)
  • cis-Dichlorodiammineplatinum(II)
  • cis-Platinum
  • Cisplatin
  • Diamminodichloride, Platinum
  • Dichlorodiammineplatinum
  • NSC-119875
  • Platidiam
  • Platino
  • Platinol
  • Platinum Diamminodichloride

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
300.05 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
298.955598 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
298.955598 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
2 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
5
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
7.6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Melting Point

270 dec °C
PhysProp

3.2.2 Solubility

2530 mg/L (at 25 °C)
AMUNDSEN,AR & STERN,EW (1982)
H2O 1 (mg/mL)
DMSO 10 (mg/mL)
10:1 PVP coprecipitate in 10% PVP 2.5 (mg/mL)
Dimethylformamide (pure anhydrous) 24 (mg/mL)

3.2.3 LogP

-2.19
HANSCH,C ET AL. (1995)

3.2.4 Stability / Shelf Life

Stability
Solution: Aqueous solutions decompose in two steps to a compound that has two water molecules replacing the two chlorine atoms. At 30°C the half life is five hours at neutral pH. The platinum compound is attacked by a variety of nucleophiles (i.e. hydroxide ion, pyridine, nitrate ion) which replace the chlorine atoms.

3.3 Chemical Classes

Other Uses -> Pharmaceuticals

3.3.1 Drugs

3.3.1.1 Human Drugs
Human drug -> Prescription; Discontinued; Active ingredient (CISPLATIN)
Human drug -> Discontinued
Cytotoxic medicines

4 Spectral Information

4.1 UV Spectra

(0.1 N HCl) max = 301 ± 2nm E= 124 - 145

4.2 Chromatograms

4.2.1 HPLC

HPLC
Column: 250 mm x 4 mm i.d. Zorbax NH2 Mobile Phase: 5% H2O in absolute EtOH Flow Rate: 2.5 mL /min Detection: UV at 210 nm Sample Preparation: 1 mg/mL in 0.1 N HCL or internal standard solution Internal Standard: guanosine (0.6 mg/mL in 0.1 N HCL) Retention Volume: 30 mL (NSC - 119875) 17.5 mL (I.S.)

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For the treatment of metastatic testicular tumors, metastatic ovarian tumors and advanced bladder cancer.

7.2 LiverTox Summary

Cisplatin is the prototype platinum coordination complex classified as an alkylating agent and used intravenously in the treatment of several forms of cancer. Cisplatin has been associated with a low rate of serum enzyme elevations and with rare cases of clinically apparent, acute liver injury.

7.3 Drug Classes

Antineoplastic Agents, Alkylating Agents

7.4 WHO Essential Medicines

Drug
Drug Classes
Cytotoxic medicines
Formulation
(1) Parenteral - General injections - unspecified: 10 mg in vial powder for injection; 50 mg in vial powder for injection; (2) Parenteral - General injections - IV: 50 mg per 50 mL; 100 mg per 100 mL; 10 mg per 10 mL; 20 mg per 20 mL
Indication
(1) Unspecified malignant neoplasms of ill-defined or unspecified sites; (2) Other specified gliomas of brain; (3) Other specified malignant neoplasms of the ovary; (4) Other specified malignant neoplasms of bronchus or lung; (5) Malignant neoplasms of nasopharynx; (6) Germ cell tumour of testis; (7) Osteosarcoma of bone and articular cartilage of unspecified sites; (8) Malignant neoplasms of lip, oral cavity or pharynx; (9) Malignant neoplasms of cervix uteri

7.5 FDA Approved Drugs

7.6 FDA Orange Book

7.7 FDA National Drug Code Directory

7.8 Drug Labels

Drug and label
Active ingredient and drug

7.9 Cancer Drugs

Drug Name
Cisplatin
FDA Approved
Yes
Drug Use

Cisplatin is approved to be used alone or with other drugs to treat:

• Bladder cancer. It is used alone in patients with advanced cancer that cannot be treated with other therapies, such as surgery or radiation therapy.

• Ovarian cancer that has spread to other parts of the body. It is used with other drugs in patients who have already had surgery or radiation therapy. It is used alone in patients whose cancer has not gotten better with standard chemotherapy and who have not received previous cisplatin.

• Testicular cancer that has spread to other parts of the body. It is used with other drugs in patients who have already had surgery or radiation therapy.

Cisplatin is also being studied in the treatment of other types of cancer.

7.10 Clinical Trials

7.10.1 ClinicalTrials.gov

7.10.2 EU Clinical Trials Register

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Cisplatin is an antineoplastic in the class of alkylating agents and is used to treat various forms of cancer. Alkylating agents are so named because of their ability to add alkyl groups to many electronegative groups under conditions present in cells. They stop tumor growth by cross-linking guanine bases in DNA double-helix strands - directly attacking DNA. This makes the strands unable to uncoil and separate. As this is necessary in DNA replication, the cells can no longer divide. In addition, these drugs add methyl or other alkyl groups onto molecules where they do not belong which in turn inhibits their correct utilization by base pairing and causes a miscoding of DNA. Alkylating agents are cell cycle-nonspecific. Alkylating agents work by three different mechanisms all of which achieve the same end result - disruption of DNA function and cell death.

8.2 MeSH Pharmacological Classification

Antineoplastic Agents
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
Cross-Linking Reagents
Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other. (See all compounds classified as Cross-Linking Reagents.)
Radiation-Sensitizing Agents
Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)

8.3 FDA Pharmacological Classification

Non-Proprietary Name
CISPLATIN
Pharmacological Classes
Platinum-containing Compounds [EXT]; Platinum-based Drug [EPC]

8.4 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XA - Platinum compounds

L01XA01 - Cisplatin

L01XA01

8.5 Absorption, Distribution and Excretion

Absorption
Following cisplatin doses of 20 to 120 mg/m^2, the concentrations of platinum are highest in liver, prostate, and kidney; somewhat lower in bladder, muscle, testicle, pancreas, and spleen; and lowest in bowel, adrenal, heart, lung, cerebrum, and cerebellum. Platinum is present in tissues for as long as 180 days after the last administration.
Route of Elimination
The parent compound, cisplatin, is excreted in the urine. Although small amounts of platinum are present in the bile and large intestine after administration of cisplatin, the fecal excretion of platinum appears to be insignificant.
Volume of Distribution
Volume of distribution at steady state = 11-12 L/m^2
Clearance

15-16 L/h/m^2 [total body clearance, 7-hour infusion of 100 mg/m^2]

62 mL/min/m^2 [renal clearance, 2-hour infusion of 100 mg/m^2]

50 mL/min/m^2 [renal clearance, 6- to 7-hour infusion of 100 mg/m^2] The renal clearance of free (ultrafilterable) platinum also exceeds the glomerular filtration rate indicating that cisplatin or other platinum-containing molecules are actively secreted by the kidneys. The renal clearance of free platinum is nonlinear and variable and is dependent on dose, urine flow rate, and individual variability in the extent of active secretion and possible tubular reabsorption.

8.6 Biological Half-Life

Cisplatin decays monoexponentially with a half life of 20 to 30 minutes following administrations of 50 or 100 mg/m^2. Cisplatin has a plasma half-life of 30 minutes. The complexes between albumin and the platinum from cisplatin do not dissociate to a significant extent and are slowly eliminated with a minimum half-life of five days or more.

8.7 Mechanism of Action

Alkylating agents work by three different mechanisms: 1) attachment of alkyl groups to DNA bases, resulting in the DNA being fragmented by repair enzymes in their attempts to replace the alkylated bases, preventing DNA synthesis and RNA transcription from the affected DNA, 2) DNA damage via the formation of cross-links (bonds between atoms in the DNA) which prevents DNA from being separated for synthesis or transcription, and 3) the induction of mispairing of the nucleotides leading to mutations.

9 Use and Manufacturing

9.1 Uses

Sources/Uses
An antineoplastic drug; [HSDB]

9.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Corrosive
Acute Toxic
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H300+H310 (21.4%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

H300 (99%): Fatal if swallowed [Danger Acute toxicity, oral]

H310 (23.3%): Fatal in contact with skin [Danger Acute toxicity, dermal]

H317 (39.8%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H318 (58.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (39.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H334 (40.8%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

H335 (11.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H340 (38.8%): May cause genetic defects [Danger Germ cell mutagenicity]

H350 (91.3%): May cause cancer [Danger Carcinogenicity]

H360 (36.9%): May damage fertility or the unborn child [Danger Reproductive toxicity]

Precautionary Statement Codes

P203, P233, P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P318, P319, P321, P330, P333+P317, P337+P317, P342+P316, P361+P364, P362+P364, P403, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 103 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 2 (99%)

Acute Tox. 2 (23.3%)

Skin Sens. 1 (39.8%)

Eye Dam. 1 (58.3%)

Eye Irrit. 2 (39.8%)

Resp. Sens. 1 (40.8%)

STOT SE 3 (11.7%)

Muta. 1B (38.8%)

Carc. 1B (91.3%)

Repr. 1B (36.9%)

10.1.3 Hazards Summary

Occupational contact urticaria documented in pharmaceutical and healthcare workers; [Kanerva, p. 219]
Kanerva - Rustemeyer L, Elsner P, John SM, Maibach HI (eds). Kanerva's Occupational Dermatology, 2nd Ed. Berlin: Springer-Verlag, 2012., p. 219

10.2 Regulatory Information

California Safe Cosmetics Program (CSCP) Reportable Ingredient

Hazard Traits - Carcinogenicity

Authoritative List - IARC Carcinogens - 2A; NTP RoC - reasonable; Prop 65

Report - regardless of intended function of ingredient in the product

11 Toxicity

11.1 Toxicological Information

11.1.1 Hepatotoxicity

The platinum compounds generally are not considered to be hepatotoxic, but cisplatin has been associated with a low rate of serum enzyme elevations during therapy. These elevations are usually mild, self-limited and asymptomatic, rarely requiring dose modification. There have been only rare case reports of clinically apparent liver injury attributed to cisplatin. In one instance, steatosis and necrosis (steatohepatitis) was found by liver biopsy in a patient who developed liver enzyme elevations 4 weeks after starting a regimen of cisplatin. In another instance, hepatocellular liver injury was described. The number of cases of liver injury attributed to cisplatin have been too few to characterize the liver injury clinically. Autoimmune and immunoallergic features have not been described and cases have all been self-limited. Cisplatin is usually given in combination with other antineoplastic agents and adverse events that occur with these combinations cannot always be attributed to cisplatin. In this regard, individual case reports of reactivation of hepatitis B, sinusoidal obstruction syndrome and severe hyperammonemic coma (without liver injury) have been described after chemotherapeutic regimens that include cisplatin and other platinum coordination complexes such as carboplatin and oxaliplatin.

Likelihood score: C (probable rare cause of clinically apparent liver injury).

11.1.2 Carcinogen Classification

IARC Carcinogenic Agent
Cisplatin
IARC Carcinogenic Classes
Group 2A: Probably carcinogenic to humans
IARC Monographs

Volume 26: (1981) Some Antineoplastic and Immunosuppressive Agents

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

Additional information
NB Overall evaluation upgraded to Group 2A with supporting evidence from other relevant data

11.1.3 Adverse Effects

IARC Carcinogen - Class 2: International Agency for Research on Cancer classifies chemicals as probable (2a), or possible (2b) human carcinogens.

NTP Carcinogen - Reasonably anticipated to be a human carcinogen.

11.1.4 Toxicity Data

ToxicityData
Human(iv): TD Lo: 2500 ug/kg
Cancer Chemotherapy Reports, 59,647,(1975)
ToxicityData
Rat(po): LD50: 25800 ,ug/kg
Yakuri to Chiryo. Pharmacology and Therapeutics, 10,723,(1982)
ToxicityData
Rat(ip): LD50: 8300 ,ug/kg
Kiso to Rinsho. Clinical Report, 15,5669,(1981)
ToxicityData
Rat(sc): LD50: 8100 ,ug/kg
Kiso to Rinsho. Clinical Report, 15,5669,(1981)
ToxicityData
Rat(iv): LD50: 8 mg/kg
Journal of the National Cancer Institute, 67,201,(1981)
ToxicityData
Rat(im): LD50: 9200 ,ug/kg
Yakuri to Chiryo. Pharmacology and Therapeutics, 10,723,(1982)
ToxicityData
Mouse(po): LD50: 32700 ug/kg
Kiso to Rinsho. Clinical Report, 15,5669,(1981)
ToxicityData
Mouse(ip): LD50: 17400 ,ug/kg
Kiso to Rinsho. Clinical Report, 15,5669,(1981)
ToxicityData
Mouse(sc): LD50: 16900 ,ug/kg
Yakuri to Chiryo. Pharmacology and Therapeutics, 10,723,(1982)
ToxicityData
Mouse(iv): LD50: 12 mg/kg
Toxicology and Applied Pharmacology, 25,230,(1973)
ToxicityData
Mouse(im): LD50: 17900 ,ug/kg
Yakuri to Chiryo. Pharmacology and Therapeutics, 10,723,(1982)
ToxicityData
Dog(iv): LD50: 2500 ,ug/kg
Toxicology and Applied Pharmacology, 25,230,(1973)
ToxicityData
Monkey(iv): LD50: 250 ,ug/kg
Cancer, 33,1219,(1974)

11.1.5 Protein Binding

Cisplatin does not undergo instantaneous and reversible binding to plasma protein that is characteristic of normal drug-protein binding. However, the platinum itself is capable of binding to plasma proteins, including albumin, transferrin, and gamma globulin. Three hours after a bolus injection and two hours after the end of a three-hour infusion, 90% of the plasma platinum is protein bound.

12 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact urticaria [Category: Skin Disease]

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Chemical Co-Occurrences in Literature

13.4 Chemical-Gene Co-Occurrences in Literature

13.5 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Chemical Co-Occurrences in Patents

14.2 Chemical-Disease Co-Occurrences in Patents

14.3 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Drug-Drug Interactions

15.4 Drug-Food Interactions

Avoid echinacea. Echinacea should be used with caution, if at all, in patients receiving therapeutic immunosuppressants. Monitor for reduced efficacy of the immunosuppressant during concomitant use.

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

18 Information Sources

  1. California Safe Cosmetics Program (CSCP) Product Database
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
  5. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  6. DailyMed
  7. LiverTox
  8. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  9. NCI Investigational Drugs
  10. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. WHO Model Lists of Essential Medicines
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) license.
    https://www.who.int/about/policies/publishing/copyright
  12. EU Clinical Trials Register
  13. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  14. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  15. International Agency for Research on Cancer (IARC)
    LICENSE
    Materials made available by IARC/WHO enjoy copyright protection under the Berne Convention for the Protection of Literature and Artistic Works, under other international conventions, and under national laws on copyright and neighbouring rights. IARC exercises copyright over its Materials to make sure that they are used in accordance with the Agency's principles. All rights are reserved.
    https://publications.iarc.fr/Terms-Of-Use
  16. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  17. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  18. NCI Cancer Drugs
  19. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  20. Protein Data Bank in Europe (PDBe)
  21. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  22. Wikidata
  23. Wikipedia
  24. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Radiation-Sensitizing Agents
    https://www.ncbi.nlm.nih.gov/mesh/68011838
  25. PubChem
CONTENTS