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Leucovorin calcium pentahydrate

PubChem CID
135802074
Structure
Leucovorin calcium pentahydrate_small.png
Leucovorin calcium pentahydrate_3D_Structure.png
Molecular Formula
Synonyms
  • Leucovorin calcium pentahydrate
  • 6035-45-6
  • Folinic acid calcium salt pentahydrate
  • Calcium folinate pentahydrate
  • Leucovorin calcium hydrate
Molecular Weight
601.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2019-01-18
  • Modify:
    2025-01-04
Description
The active metabolite of FOLIC ACID. Leucovorin is used principally as an antidote to FOLIC ACID ANTAGONISTS.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Leucovorin calcium pentahydrate.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

calcium;(2S)-2-[[4-[(2-amino-5-formyl-4-oxo-3,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioate;pentahydrate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C20H23N7O7.Ca.5H2O/c21-20-25-16-15(18(32)26-20)27(9-28)12(8-23-16)7-22-11-3-1-10(2-4-11)17(31)24-13(19(33)34)5-6-14(29)30;;;;;;/h1-4,9,12-13,22H,5-8H2,(H,24,31)(H,29,30)(H,33,34)(H4,21,23,25,26,32);;5*1H2/q;+2;;;;;/p-2/t12?,13-;;;;;;/m0....../s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

NPPBLUASYYNAIG-ZIGBGYJWSA-L
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1C(N(C2=C(N1)N=C(NC2=O)N)C=O)CNC3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)[O-])C(=O)[O-].O.O.O.O.O.[Ca+2]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H31CaN7O12
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

6035-45-6
41927-89-3

2.3.3 Deprecated CAS

41927-89-3

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 KEGG ID

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 5 Formyltetrahydrofolate
  • 5 Formyltetrahydropteroylglutamate
  • 5-Formyltetrahydrofolate
  • 5-Formyltetrahydropteroylglutamate
  • Acid, Folinic
  • Calcium Folinate
  • Calcium Leucovorin
  • Citrovorum Factor
  • Factor, Citrovorum
  • Folinate, Calcium
  • Folinic Acid
  • Folinic Acid SF
  • Folinic Acid-SF
  • Leucovorin
  • Leucovorin, (D)-Isomer
  • Leucovorin, (DL)-Isomer
  • Leucovorin, (R)-Isomer
  • Leucovorin, Calcium
  • Leucovorin, Calcium (1:1) Salt
  • Leucovorin, Calcium (1:1) Salt, (DL)-Isomer
  • Leucovorin, Calcium (1:1) Salt, Pentahydrate
  • Leucovorin, Monosodium Salt
  • Leukovorin
  • Leukovorum
  • Monosodium Salt Leucovorin
  • N(5)-Formyltetrahydrofolate
  • Wellcovorin

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
601.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
15
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
601.1656603 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
601.1656603 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
226Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
40
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
900
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
1
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
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
7
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Antidotes; Vitamin B Complex; Vitamins
Human drug -> Discontinued

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Antidotes; Vitamin B Complex; Vitamins

6.2 Clinical Trials

6.2.1 EU Clinical Trials Register

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Antidotes
Agents counteracting or neutralizing the action of POISONS. (See all compounds classified as Antidotes.)
Vitamin B Complex
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

8 Use and Manufacturing

8.1 Uses

Use (kg; approx.) in Germany (2009): >10

Consumption (g per capita; approx.) in Germany (2009): 0.000122

Calculated removal (%): 22

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H319 (97.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H334 (97.5%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]

H335 (97.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P233, P260, P261, P264, P264+P265, P271, P272, P280, P284, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P342+P316, 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 40 reports by companies from 3 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.

9.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Skin Sens. 1 (100%)

Eye Irrit. 2 (97.5%)

Resp. Sens. 1 (97.5%)

STOT SE 3 (97.5%)

Skin Irrit. 2 (100%)

Skin Sens. 1A (100%)

Eye Irrit. 2 (100%)

Resp. Sens. 1A (100%)

STOT SE 3 (100%)

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: L-Glutamic acid, N-[4-[[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-, calcium salt(1:1), pentahydrate

10 Toxicity

10.1 Toxicological Information

10.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Leucovorin (folinic acid; 5-formyltetrahydrofolic acid) and its levo- isomer, levoleucovorin, are folic acid derivatives that are normal components of breastmilk. Because leucovorin and levoleucovorin are used as therapeutic agents with potentially toxic drugs such as fluorouracil or methotrexate, the LactMed record of the drug it is used with should be consulted.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Gene Co-Occurrences in Literature

11.5 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 Chemical Co-Occurrences in Patents

12.3 Chemical-Disease Co-Occurrences in Patents

12.4 Chemical-Gene Co-Occurrences in Patents

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 ChemIDplus

14.3 UN GHS Classification

14.4 EPA DSSTox Classification

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    L-Glutamic acid, N-[4-[[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl)methyl]amino]benzoyl]-, calcium salt(1:1), pentahydrate
    https://services.industrialchemicals.gov.au/search-inventory/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  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. FDA Global Substance Registration System (GSRS)
    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
  6. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  7. Drugs and Lactation Database (LactMed)
  8. 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
  9. EU Clinical Trials Register
  10. 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
  11. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    SODIUM FOLINATE
  12. Wikidata
    leucovorin calcium pentahydrate
    https://www.wikidata.org/wiki/Q27287765
  13. 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
  14. PubChem
  15. GHS Classification (UNECE)
CONTENTS