Clinprost

• CAT Number: I024914
• CAS Number: 88931-51-5
• Molecular Formula: C22H36O4
• Molecular Weight: 364.53
• Purity: 98%
• Synonyms: Clinprost; TEI 9090; TEI9090; TEI-9090; TTC909; TTC-909; TTC 909
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (+)-Methyl-(3aS,5R,6R,6aS)-1,3a,4,5,6,6a-hexahydro-5-hydroxy-6-((E)-(3S)-3-hydroxy-1-octenyl)-2-pentalenevalerate
• InChI: InChI=1S/C22H36O4/c1-3-4-5-9-18(23)11-12-19-20-14-16(13-17(20)15-21(19)24)8-6-7-10-22(25)26-2/h11-13,17-21,23-24H,3-10,14-15H2,1-2H3/b12-11+/t17-,18-,19+,20-,21+/m0/s1
• InChIKey: QIGRQPVOWVHYBT-KABTVRTISA-N
• SMILES: O=C(OC)CCCCC1=C[C@@]2([H])C[C@@H](O)[C@H](/C=C/[C@@H](O)CCCCC)[C@@]2([H])C1

Clinprost is a Vasodilator (peripheral), Platelet aggregation inhibitor, and Prostaglandin I2 receptor agonist

Reference

1: Umekubo N, Hayashi Y. Pot-Economical Total Synthesis of Clinprost. Org Lett. 2020 Dec 4;22(23):9365-9370. doi: 10.1021/acs.orglett.0c03616. Epub 2020 Nov 24. PMID: 33231082.
2: Minagawa T, Sakanaka K, Inaba S, Sai Y, Tamai I, Suwa T, Tsuji A. Blood- brain-barrier transport of lipid microspheres containing clinprost, a prostaglandin I2 analogue. J Pharm Pharmacol. 1996 Oct;48(10):1016-22. doi: 10.1111/j.2042-7158.1996.tb05893.x. PMID: 8953502.
3: Cacione DG, Macedo CR, Baptista-Silva JC. Pharmacological treatment for Buerger’s disease. Cochrane Database Syst Rev. 2016 Mar 11;3(3):CD011033. doi: 10.1002/14651858.CD011033.pub3. Update in: Cochrane Database Syst Rev. 2020 May 4;5:CD011033. PMID: 26967103; PMCID: PMC7104255.
4: Cacione DG, Macedo CR, do Carmo Novaes F, Baptista-Silva JC. Pharmacological treatment for Buerger’s disease. Cochrane Database Syst Rev. 2020 May 4;5(5):CD011033. doi: 10.1002/14651858.CD011033.pub4. PMID: 32364620; PMCID: PMC7197514.
5: Nagy EE, Hyatt IF, Gettys KE, Yeazell ST, Frempong SK Jr, Croatt MP. Sequential Pd(0)-, Rh(I)-, and Ru(II)-catalyzed reactions in a nine-step synthesis of clinprost. Org Lett. 2013 Feb 1;15(3):586-9. doi: 10.1021/ol303402e. Epub 2013 Jan 17. PMID: 23327495.
6: Cacione DG, Baptista-Silva JC, Macedo CR. Pharmacological treatment for Buerger’s disease. Cochrane Database Syst Rev. 2016 Feb 1;2:CD011033. doi: 10.1002/14651858.CD011033.pub2. Update in: Cochrane Database Syst Rev. 2016;3:CD011033. PMID: 26828199.
7: Karasawa Y, Hitomi T, Komiyama H, Isobe Y, Kobayashi T, Yoshida S, Nakaike S, Araki H. Effect of TTC-909 in a middle cerebral artery thrombosis model in stroke-prone spontaneously hypertensive rats. Eur J Pharmacol. 2002 Aug 2;449(1-2):127-133. doi: 10.1016/s0014-2999(02)01945-3. PMID: 12163116.
8: Yae T, Araki H, O-ogami Y, Iwasaki K, Tanabe H, Fujiwara M. Effects of the isocarbacyclin methyl ester clinprost incorporated into lipid microspheres, in focal ischemia of stroke-prone spontaneously hypertensive rats. Arzneimittelforschung. 1997 Nov;47(11):1200-3. PMID: 9428973.
9: Karasawa Y, Komiyama H, Yoshida S, Hino N, Katsuura Y, Nakaike S, Araki H. Effect of TTC-909 on cerebral infarction following permanent occlusion of the middle cerebral artery in stroke prone spontaneously hypertensive rats. J Pharmacol Sci. 2003 Apr;91(4):305-12. doi: 10.1254/jphs.91.305. PMID: 12719659.
10: Matsuda S, Wen TC, Karasawa Y, Araki H, Otsuka H, Ishihara K, Sakanaka M. Protective effect of a prostaglandin I2 analog, TEI-7165, on ischemic neuronal damage in gerbils. Brain Res. 1997 Sep 26;769(2):321-8. doi: 10.1016/s0006-8993(97)00724-5. PMID: 9374201.