Ciprostene Calcium
Basic information
- CAS
81703-55-1- Standard SMILES
CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@]2(C)C/C(=C\CCCC(=O)[O-])C[C@H]12.CCCCC[C@H](O)/C=C/[C@H]1[C@H](O)C[C@]2(C)C/C(=C\CCCC(=O)[O-])C[C@H]12.[Ca+2]- InChIKey
SIHLLVRXCZZNOX-ZMLBHFFASA-N- Molecular formula
- C44H70CaO8
- Average molar mass
- 767.1 g/mol
- Monoisotopic mass
- 766.46966
Overview
See also: Ciprostene (has active moiety).
Names & identifiers
- Preferred name
- Ciprostene Calcium
- IUPAC
- calcium bis((5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-6a-methyl-1,3,3a,4,5,6-hexahydropentalen-2-ylidene]pentanoate)
- English name
- 6,9ALPHA-METHYLENE-9BETA-METHYL-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID, CALCIUM SALT
- Molecular formula
- C22H38CaO4
- Molecular weight
- 406.62
Names & synonyms
CIPROSTENE CALCIUMCiprostene calcium [USAN]9-beta-MethylcarbacyclinUNII-A85Y5Y98EJ81703-55-1A85Y5Y98EJU-61,431FCiprostene calcium (USAN)U 61431FU-61431FCIPROSTENE CALCIUM [MART.]Calcium (Z)-(3aS,5R,6R,6aR)-hexahydro-5-hydroxy-6-((E)-(3S)-3-hydroxy-1-octenyl)-3a-methyl-delta(sup 2)(1H),delta-pentalenevalerate (1:2)
Show more names
CIPROSTENE CALCIUM SALTWKRNCYQUQFBOCZ-FCIOBEBZSA-Mpentalenylidene)-,calciumsalt(2:1),(3as-(2z,3a-alpha,5-beta,6-alpha(1e,3r*5-(hexahydro-5-hydroxy-6-(3-hydroxy-1-octenyl)-3a-methyl-2(1h)-pentanoicaci6,9ALPHA-METHYLENE-9BETA-METHYL-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-OIC ACID, CALCIUM SALT
CIPROSTENE CALCIUM (MART.)CALCIUM (Z)-(3AS,5R,6R,6AR)-HEXAHYDRO-5-HYDROXY-6-((E)-(3S)-3-HYDROXY-1-OCTENYL)-3A-METHYL-.DELTA.(SUP 2)(1H),.DELTA.-PENTALENEVALERATE (1:2)Pentanoic acid, 5-(hexahydro-5-hydroxy-6-(3-hydroxy-1-octenyl)-3a-methyl-2(1H)-pentalenylidene)-, calcium salt (2:1), (3aS-(2Z,3aalpha,5beta,6alpha(1E,3R*),6aalpha))-RefChem:126331Ciprostene (calcium salt)calcium;(5Z)-5-[(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxyoct-1-enyl]-6a-methyl-1,3,3a,4,5,6-hexahydropentalen-2-ylidene]pentanoateSCHEMBL667640CHEMBL2106497
Properties
Computed structural properties
- Topological polar surface area
- 161 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 18
- Heavy atoms
- 53
- Formal charge
- 0
- Complexity
- 519
Physicochemical properties
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 25 mg/ml; · DMF: > 25 mg/ml; DMSO: > 16.8 mg/ml; ethanol: > 34 mg/ml; PBS pH 7.2: > 0.29 μg/ml
- form
- A crystalline solid
- FDA UNII
- 85 Y5Y98EJ · A85Y5Y98EJ
Chemistry & industry
Applications
DescriptionCiprostene is the 9β-methyl analog of carbaprostacyclin and a stable analog of PGI2. Ciprostene exhibits biological activity similar to PGI2, but is 30-fold less potent. In patas monkeys, ciprostene induces hypotension and causes tachycardia when administered at a dose of 0.16 μg/kg/min. In addition, ciprostene inhibits ADP-induced platelet aggregation ex vivo and in vitro with ID50 values of 9.1 μg/kg/min and 60 ng/ml, respectively.
UsesPlatelet aggregation inhibitor.
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