ID: ALA5314377

Max Phase: Approved

First Approval: 1999

Molecular Formula: C84H121ClN18O17

Molecular Weight: 1570.35

Molecule Type: Protein

Representations

Synonyms (4): Ganirelix acetate | Ganirest | RS-26306 | RS-26306-298
Synonyms from Alternative Forms(4):

Trade Names(2): Ganirelix acetate | Orgalutran

Canonical SMILES:  CC(=O)O.CC(=O)O.CC/N=C(\NCC)NCCCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCCCN/C(=N/CC)NCC)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(Cl)cc1)NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(C)=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O

Standard InChI:  InChI=1S/C80H113ClN18O13.2C2H4O2/c1-9-84-79(85-10-2)88-38-17-15-24-60(70(104)94-62(41-49(5)6)71(105)93-61(25-16-18-39-89-80(86-11-3)87-12-4)78(112)99-40-20-26-68(99)77(111)90-50(7)69(82)103)92-73(107)64(44-53-30-35-59(102)36-31-53)97-76(110)67(48-100)98-75(109)66(46-55-21-19-37-83-47-55)96-74(108)65(43-52-28-33-58(81)34-29-52)95-72(106)63(91-51(8)101)45-54-27-32-56-22-13-14-23-57(56)42-54;2*1-2(3)4/h13-14,19,21-23,27-37,42,47,49-50,60-68,100,102H,9-12,15-18,20,24-26,38-41,43-46,48H2,1-8H3,(H2,82,103)(H,90,111)(H,91,101)(H,92,107)(H,93,105)(H,94,104)(H,95,106)(H,96,108)(H,97,110)(H,98,109)(H2,84,85,88)(H2,86,87,89);2*1H3,(H,3,4)/t50-,60-,61+,62+,63-,64+,65-,66-,67+,68+;;/m1../s1

Standard InChI Key:  OVBICQMTCPFEBS-SATRDZAXSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: Yes

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Properties

Molecular Weight: 1570.35

Molecular Weight (Monoisotopic): 1568.8423

AlogP:

#Rotatable Bonds:

Polar Surface Area:

Molecular Species:

HBA:

HBD:

#RO5 Violations:

HBA (Lipinski):

HBD (Lipinski):

#RO5 Violations (Lipinski):

CX Acidic pKa:

CX Basic pKa:

CX LogP:

CX LogD:

Aromatic Rings:

Heavy Atoms:

QED Weighted:

Np Likeness Score:

References

1. Jiang G, Stalewski J, Galyean R, Dykert J, Schteingart C, Broqua P, Aebi A, Aubert ML, Semple G, Robson P, Akinsanya K, Haigh R, Riviere P, Trojnar J, Junien JL, Rivier JE..  (2001)  GnRH antagonists: a new generation of long acting analogues incorporating p-ureido-phenylalanines at positions 5 and 6.,  44  (3): [PMID:11462984] [10.1021/jm0003900]

2. Unpublished dataset, 

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. WHO Anatomical Therapeutic Chemical Classification, 

5. British National Formulary (72nd edition), 

6. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

7. Unpublished dataset, 

8. European Medicines Agency, 

Source

Source(7):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• European Medicines Agency