(2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-5-(carbamoylamino)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]pentanamido]-4-methylpentanamide; acetic acid

• ChemBase ID: 154766
• Molecular Formular: C72H96ClN17O16
• Molecular Mass: 1491.08994
• Monoisotopic Mass: 1489.69094776
• SMILES: C[C@H](C(=O)N)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCCNC(=O)N)NC(=O)[C@H](Cc1ccc(cc1)O)NC(=O)[C@H](CO)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(cc1)Cl)NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(=O)C.CC(=O)O
• Canonical SMILES: CC(=O)O.OC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)N)C)CCCNC(=N)N)CC(C)C)CCCNC(=O)N)Cc1ccc(cc1)O)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(cc1)Cl)NC(=O)[C@@H](Cc1ccc2c(c1)cccc2)NC(=O)C
• InChI: InChI=1S/C70H92ClN17O14.C2H4O2/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44;1-2(3)4/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102);1H3,(H,3,4)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+;/m1./s1
• InChIKey: KFEFLCOCAHJBEA-ANRVCLKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-5-(carbamoylamino)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]pentanamido]-4-methylpentanamide; acetic acid
• IUPAC Traditional name: acetic acid; cetrorelix
• Synonyms: Cetrotide; N-acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N5-(aminocarbonyl)-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide acetic acid salt; NS-75A; SB-75; Cetrorelix acetate

Database IDs

• CAS Number: 145672-81-7
• MDL Number: MFCD08459466
• PubChem SID: 162248904
• PubChem CID: 25078429

CALCULATED PROPERTIES

• Acid pKa: 9.491455
• H Acceptors: 18
• H Donor: 17
• LogD (pH = 5.5): -3.719707
• LogD (pH = 7.4): -3.3502734
• Log P: -1.7055382
• Molar Refractivity: 384.1588 cm^3
• Polarizability: 146.09546 Å^3
• Polar Surface Area: 495.67 Å^2
• Rotatable Bonds: 38
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: methanol: soluble10%
• Apperance: solid

Safety Information

• German water hazard class: 3
• Risk Statements: 60-63
• Safety Statements: 22
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C70H92ClN17O14 · xC2H4O2

DETAILS

Sigma Aldrich - C5249

Biochem/physiol Actions
Cetrorelix acetate is a luteinizing hormone releasing hormone receptor antagonist. It causes prepubertal reduction in bone modeling, bone density and bone strength comparable to post-menopausal bone loss.1