An official website of the United States government

H-DL-Tyr-DL-Ala-DL-Asp-DL-Ala-DL-xiIle-DL-Phe-DL-xiThr-DL-Asn-DL-Ser-DL-Tyr-DL-Arg-DL-Lys-DL-Val-DL-Leu-Gly-DL-Gln-DL-Leu-DL-Ser-DL-Ala-DL-Arg-DL-Lys-DL-Leu-DL-Leu-DL-Gln-DL-Asp-DL-xiIle-DL-Met-DL-Ser-DL-Arg-NH2

PubChem CID
16129620
Structure
H-DL-Tyr-DL-Ala-DL-Asp-DL-Ala-DL-xiIle-DL-Phe-DL-xiThr-DL-Asn-DL-Ser-DL-Tyr-DL-Arg-DL-Lys-DL-Val-DL-Leu-Gly-DL-Gln-DL-Leu-DL-Ser-DL-Ala-DL-Arg-DL-Lys-DL-Leu-DL-Leu-DL-Gln-DL-Asp-DL-xiIle-DL-Met-DL-Ser-DL-Arg-NH2_small.png
Molecular Formula
Synonyms
  • SERMORELIN
  • 86168-78-7
  • Sermorelin (INN)
  • CHEBI:9118
  • D08509
Molecular Weight
3357.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2007-07-03
  • Modify:
    2025-01-18
Description
Sermorelin is a 29 amino acid polypeptide that is used to treat growth problems (usually in children) due to growth hormone deficiency. It is the biologically active fragment of human growth hormone-releasing factor (GHRH). It has a role as a diagnostic agent. It is a polypeptide and a peptide hormone.
Sermorelin acetate is the acetate salt of an amidated synthetic 29-amino acid peptide (GRF 1-29 NH 2 ) that corresponds to the amino-terminal segment of the naturally occurring human growth hormone-releasing hormone (GHRH or GRF) consisting of 44 amino acid residues
The biologically active fragment of human growth hormone-releasing factor, consisting of GHRH(1-29)-amide. This N-terminal sequence is identical in several mammalian species, such as human, pig, and cattle. It is used to diagnose or treat patients with GROWTH HORMONE deficiency.
See also: Sermorelin (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
H-DL-Tyr-DL-Ala-DL-Asp-DL-Ala-DL-xiIle-DL-Phe-DL-xiThr-DL-Asn-DL-Ser-DL-Tyr-DL-Arg-DL-Lys-DL-Val-DL-Leu-Gly-DL-Gln-DL-Leu-DL-Ser-DL-Ala-DL-Arg-DL-Lys-DL-Leu-DL-Leu-DL-Gln-DL-Asp-DL-xiIle-DL-Met-DL-Ser-DL-Arg-NH2.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible, too many undefined stereo centers

2 Biologic Description

SVG Image
SVG Image
IUPAC Condensed
H-DL-Tyr-DL-Ala-DL-Asp-DL-Ala-DL-xiIle-DL-Phe-DL-xiThr-DL-Asn-DL-Ser-DL-Tyr-DL-Arg-DL-Lys-DL-Val-DL-Leu-Gly-DL-Gln-DL-Leu-DL-Ser-DL-Ala-DL-Arg-DL-Lys-DL-Leu-DL-Leu-DL-Gln-DL-Asp-DL-xiIle-DL-Met-DL-Ser-DL-Arg-NH2
Sequence
YADAXFXNSYRKVLGQLSARKLLQDXMSR
HELM
PEPTIDE1{(Y,[dY]).(A,[dA]).(D,[dD]).(A,[dA]).[*C(=O)C(C(C)CC)N* |$_R2;;;;;;;;;_R1$|].(F,[dF]).[*C(=O)C(C(C)O)N* |$_R2;;;;;;;;_R1$|].(N,[dN]).(S,[dS]).(Y,[dY]).(R,[dR]).(K,[dK]).(V,[dV]).(L,[dL]).G.(Q,[dQ]).(L,[dL]).(S,[dS]).(A,[dA]).(R,[dR]).(K,[dK]).(L,[dL]).(L,[dL]).(Q,[dQ]).(D,[dD]).[*C(=O)C(C(C)CC)N* |$_R2;;;;;;;;;_R1$|].(M,[dM]).(S,[dS]).(R,[dR]).[am]}$$$$V2.0
IUPAC
DL-tyrosyl-DL-alanyl-DL-alpha-aspartyl-DL-alanyl-DL-isoleucyl-DL-phenylalanyl-DL-threonyl-DL-asparagyl-DL-seryl-DL-tyrosyl-DL-arginyl-DL-lysyl-DL-valyl-DL-leucyl-glycyl-DL-glutaminyl-DL-leucyl-DL-seryl-DL-alanyl-DL-arginyl-DL-lysyl-DL-leucyl-DL-leucyl-DL-glutaminyl-DL-alpha-aspartyl-DL-isoleucyl-DL-methionyl-DL-seryl-DL-argininamide

3 Names and Identifiers

3.1 Computed Descriptors

3.1.1 IUPAC Name

4-[[1-[[1-[[1-[[1-[[4-amino-1-[[1-[[1-[[1-[[6-amino-1-[[1-[[1-[[2-[[5-amino-1-[[1-[[1-[[1-[[1-[[6-amino-1-[[1-[[1-[[5-amino-1-[[1-[[1-[[1-[[1-[(1-amino-5-carbamimidamido-1-oxopentan-2-yl)amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-carboxy-1-oxopropan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-oxoethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]amino]-5-carbamimidamido-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-3-[2-[[2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoylamino]-4-oxobutanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

3.1.2 InChI

InChI=1S/C149H246N44O42S/c1-20-77(13)116(191-122(211)81(17)168-132(221)104(66-113(204)205)178-121(210)79(15)167-123(212)88(152)62-84-39-43-86(198)44-40-84)145(234)185-102(63-83-32-23-22-24-33-83)138(227)193-118(82(18)197)146(235)186-103(65-111(155)202)137(226)189-108(71-196)142(231)182-101(64-85-41-45-87(199)46-42-85)136(225)175-93(38-31-56-165-149(161)162)126(215)174-91(35-26-28-53-151)131(220)190-115(76(11)12)143(232)184-97(58-72(3)4)124(213)166-68-112(203)170-94(47-49-109(153)200)128(217)180-100(61-75(9)10)135(224)188-106(69-194)140(229)169-80(16)120(209)172-92(37-30-55-164-148(159)160)125(214)173-90(34-25-27-52-150)127(216)179-99(60-74(7)8)134(223)181-98(59-73(5)6)133(222)176-95(48-50-110(154)201)129(218)183-105(67-114(206)207)139(228)192-117(78(14)21-2)144(233)177-96(51-57-236-19)130(219)187-107(70-195)141(230)171-89(119(156)208)36-29-54-163-147(157)158/h22-24,32-33,39-46,72-82,88-108,115-118,194-199H,20-21,25-31,34-38,47-71,150-152H2,1-19H3,(H2,153,200)(H2,154,201)(H2,155,202)(H2,156,208)(H,166,213)(H,167,212)(H,168,221)(H,169,229)(H,170,203)(H,171,230)(H,172,209)(H,173,214)(H,174,215)(H,175,225)(H,176,222)(H,177,233)(H,178,210)(H,179,216)(H,180,217)(H,181,223)(H,182,231)(H,183,218)(H,184,232)(H,185,234)(H,186,235)(H,187,219)(H,188,224)(H,189,226)(H,190,220)(H,191,211)(H,192,228)(H,193,227)(H,204,205)(H,206,207)(H4,157,158,163)(H4,159,160,164)(H4,161,162,165)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.3 InChIKey

WGWPRVFKDLAUQJ-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

3.1.4 SMILES

CCC(C)C(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(C(C)O)C(=O)NC(CC(=O)N)C(=O)NC(CO)C(=O)NC(CC2=CC=C(C=C2)O)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(C(C)C)C(=O)NC(CC(C)C)C(=O)NCC(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)C(=O)NC(CO)C(=O)NC(C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(CCC(=O)N)C(=O)NC(CC(=O)O)C(=O)NC(C(C)CC)C(=O)NC(CCSC)C(=O)NC(CO)C(=O)NC(CCCNC(=N)N)C(=O)N)NC(=O)C(C)NC(=O)C(CC(=O)O)NC(=O)C(C)NC(=O)C(CC3=CC=C(C=C3)O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

3.2 Molecular Formula

C149H246N44O42S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

3.3 Other Identifiers

3.3.1 CAS

86168-78-7

3.3.2 ChEBI ID

3.3.3 DrugBank ID

3.3.4 HMDB ID

3.3.5 NCI Thesaurus Code

3.3.6 PharmGKB ID

3.3.7 Wikipedia

3.4 Synonyms

3.4.1 MeSH Entry Terms

  • Geref
  • GHRH(1-29)NH2
  • GRF(1-29)NH2
  • Growth Hormone-Releasing Factor(1-29)Amide
  • hGHRH(1-29)NH2
  • Sermorelin
  • Sermorelin Acetate
  • Somatotropin-Releasing-Hormone(1-29)Amide

3.4.2 Depositor-Supplied Synonyms

4 Chemical and Physical Properties

4.1 Computed Properties

Property Name
Molecular Weight
Property Value
3357.9 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
-12.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
52
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
49
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
118
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
3356.8220541 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
3355.8186992 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
1470 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
236
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
7640
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
31
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
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4.2 Experimental Properties

4.2.1 Hydrophobicity

-0.33

4.2.2 Isoelectric Point

9.99

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

For the treatment of dwarfism, prevention of HIV-induced weight loss

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Sermorelin is used in the treatment of children with growth hormone deficiency or growth failure. Geref increases plasma growth hormone (GH) concentration by stimulating the pituitary gland to release GH. Geref is similar to the full-length native hormone (44 residues) in its ability to stimulate GH secretion in humans.

8.2 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H01 - Pituitary and hypothalamic hormones and analogues

H01A - Anterior pituitary lobe hormones and analogues

H01AC - Somatropin and somatropin agonists

H01AC04 - Sermorelin

V - Various

V04 - Diagnostic agents

V04C - Other diagnostic agents

V04CD - Tests for pituitary function

V04CD03 - Sermorelin

8.3 Biological Half-Life

11-12 min

8.4 Mechanism of Action

Sermorelin binds to the growth hormone releasing hormone receptor and mimics native GRF in its ability to stimulate growth hormone secretion.

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Chemical Co-Occurrences in Literature

9.5 Chemical-Gene Co-Occurrences in Literature

9.6 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

11 Biological Test Results

11.1 BioAssay Results

12 Classification

12.1 MeSH Tree

12.2 ChEBI Ontology

12.3 KEGG: ATC

12.4 KEGG: Target-based Classification of Drugs

12.5 WHO ATC Classification System

13 Information Sources

  1. ChEBI
  2. 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
  3. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  4. 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
  5. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  6. Springer Nature
  7. 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/
  8. Wikipedia
  9. 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
  10. PubChem
  11. 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
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  12. PATENTSCOPE (WIPO)
CONTENTS