Carboprost

Base Information

• Chemical Name: Carboprost
• CAS No.: 35700-23-3
• Molecular Formula: C21H36O5
• Molecular Weight: 368.514
• UNII: 7B5032XT6O
• ChEMBL ID: CHEMBL1237122
• DSSTox Substance ID: DTXSID4022739
• Metabolomics Workbench ID: 2441
• NCI Thesaurus Code: C61662
• Nikkaji Number: J17.442D
• Pharos Ligand ID: DPSJ5FBD5ZYB
• RXCUI: 2051
• Wikidata: Q5038067
• Wikipedia: Carboprost
• Mol file: 35700-23-3.mol

Synonyms:15 Methylprostaglandin F2alpha;15(S)-15-Methyl PGF2alpha;15-Methylprostaglandin F2alpha;Carboprost

Chemical Property of Carboprost

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 1.71E-13mmHg at 25°C
• Melting Point: 79-82 °C
• Refractive Index: 1.569
• Boiling Point: 536.562 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 292.373 °C
• PSA: 97.99000
• Density: 1.139 g/cm³
• LogP: 3.43300
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 368.25627424
• Heavy Atom Count: 26
• Complexity: 473

Purity/Quality:

99% ^*data from raw suppliers

15(S)-15-methyl Prostaglandin F2α ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C)(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
• Recent ClinicalTrials: Second-Line Uterotonics in Postpartum Hemorrhage: A Randomized Clinical Trial
• Description: 15(S)-15-methyl PGF2α is a metabolically stable analog of PGF2α. It is a potent uterine stimulant and abortifacient which can be administered intramuscularly to induce labor. It induces luteolysis and reduces serum progesterone concentrations when given as an intramuscular injection in non-pregnant rhesus monkeys.
• Uses: Analog of prostaglandin F2α. Oxytocic. Analog of prostaglandin F2a. Oxytocic

Technology Process of Carboprost

There total 59 articles about Carboprost which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

U 36384 (35700-21-1) → Carboprost (35700-23-3)

Guidance literature:

With water; sodium hydroxide; In methanol;

Reference yield: 85.0%

C27H50O5Si → Carboprost (35700-23-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield: 85.0%

C30H56O5Si → Carboprost (35700-23-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

upstream raw materials:

(15S)-15-methyl-PGF_2α 1,11-lactone 9,15-bis(tert-butyldimethylsilyl ether)

(15S)-15-methyl prostaglandin F_2α methyl ester

(15S)-15-methyl-PGF_2α methyl ester 11-(trichloroethylcarbonate)

(15S)-15-methyl-PGF_2α methyl ester 9,15bis(tert-butyldimethylsilyl ether)

Downstream raw materials:

U 36384

(15S)-15-methyl-9-deoxy-Δ⁹-PGD₂

(15S)-15-methyl-PGD₂

(15S)-15-methyl-PGF_2α 1,9-lactone

Refernces

• 1、 Zhang, Fuhao,Zeng, Jingwen,Gao, Mohan,Wang, Linzhou,Chen, Gen-Qiang,Lu, Yixin,Zhang, Xumu. "Concise, scalable and enantioselective total synthesis of prostaglandins". . p. 692 - 697. Retrieved 2021/06/01.
• 2、 -. "Method for separating prostaglandin isomer (by machine translation)". Paragraph 0035; 0041-0043. . Retrieved 2020/02/19.