Chemistry:Colforsin daropate

Colforsin daropate
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	none;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name [(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-acetyloxy-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-5,6,6a,8,9,10-hexahydro-2H-benzo[f]chromen-6-yl] 3-dimethylaminopropanoate;
CAS Number	113462-26-3 ; HCl: 138605-00-2 ;
PubChem CID	444029; HCl: 444028;
ChemSpider	392052 ; HCl: 392051;
UNII	1196KQZ976; HCl: C6P4R272GT;
KEGG	HCl: D01697;
CompTox Dashboard (EPA)	DTXSID20150415; HCl: DTXSID90930165;
Chemical and physical data
Formula	C27H43NO8
Molar mass	509.640 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)O[C@H]1[C@H]([C@H]2C(CC[C@@H]([C@@]2([C@@]3([C@@]1(O[C@@](CC3=O)(C)C=C)C)O)C)O)(C)C)OC(=O)CCN(C)C;
	InChI InChI=1S/C27H43NO8/c1-10-24(5)15-18(31)27(33)25(6)17(30)11-13-23(3,4)21(25)20(35-19(32)12-14-28(8)9)22(34-16(2)29)26(27,7)36-24/h10,17,20-22,30,33H,1,11-15H2,2-9H3/t17-,20-,21-,22-,24-,25-,26+,27-/m0/s1 ; Key:RSOZZQTUMVBTMR-XGUNBQNXSA-N ;
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Short description: Chemical compound

Colforsin daropate is a cardiovascular drug used to treat acute heart failure.^[1] Chemically, it is a carboxylic ester derived from the condensation of forskolin (colforsin) with N,N-dimethyl-β-alanine.^[2]

Its water-soluble hydrochloride salt (NKH 477)^[3] is an adenylyl cyclase activator which has been studied for its cardiac selectivity.^[4]^[5]

Colforsin daropate has been studied for its potential to be repurposed for the treatment of some types of cancer.^[6]

References

↑ "Colforsin daropate". AdisInsight. https://adisinsight.springer.com/drugs/800001302.
↑ "colforsin daropate". EMBL-EBI. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:166826.
↑ "β-Alanine, N,N-dimethyl-, (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyldodecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho[2,1-bpyran-6-yl ester, hydrochloride (1:1)"]. American Chemical Society. https://commonchemistry.cas.org/detail?cas_rn=138605-00-2.
↑ "Effect of NKH477, a new water-soluble forskolin derivative, on arterial-ventricular coupling and mechanical energy transduction in patients with left ventricular systolic dysfunction: comparison with dobutamine". Journal of Cardiovascular Pharmacology 24 (2): 310–316. August 1994. doi:10.1097/00005344-199424020-00018. PMID 7526066.
↑ "Effects of NKH477, a water-soluble forskolin derivative, on cardiac function in rats with chronic heart failure after myocardial infarction". The Journal of Pharmacology and Experimental Therapeutics 274 (1): 120–126. July 1995. doi:10.1016/S0022-3565(25)10521-1. PMID 7616388.
↑ "Repurposing colforsin daropate to treat MYC-driven high-grade serous ovarian carcinomas". Science Signaling 17 (863). November 2024. doi:10.1126/scisignal.ado8303. PMID 39561220.

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Original source: https://en.wikipedia.org/wiki/Colforsin daropate. Read more

[1] "Colforsin daropate". AdisInsight. https://adisinsight.springer.com/drugs/800001302.

[2] "colforsin daropate". EMBL-EBI. https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:166826.

[3] "β-Alanine, N,N-dimethyl-, (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyldodecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho[2,1-bpyran-6-yl ester, hydrochloride (1:1)"]. American Chemical Society. https://commonchemistry.cas.org/detail?cas_rn=138605-00-2.

[4] "Effect of NKH477, a new water-soluble forskolin derivative, on arterial-ventricular coupling and mechanical energy transduction in patients with left ventricular systolic dysfunction: comparison with dobutamine". Journal of Cardiovascular Pharmacology 24 (2): 310–316. August 1994. doi:10.1097/00005344-199424020-00018. PMID 7526066.

[5] "Effects of NKH477, a water-soluble forskolin derivative, on cardiac function in rats with chronic heart failure after myocardial infarction". The Journal of Pharmacology and Experimental Therapeutics 274 (1): 120–126. July 1995. doi:10.1016/S0022-3565(25)10521-1. PMID 7616388.

[6] "Repurposing colforsin daropate to treat MYC-driven high-grade serous ovarian carcinomas". Science Signaling 17 (863). November 2024. doi:10.1126/scisignal.ado8303. PMID 39561220.

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v t e Xenobiotic-sensing receptor modulators
CAR	Agonists: 6,7-Dimethylesculetin Amiodarone Artemisinin Benfuracarb Carbamazepine Carvedilol Chlorpromazine Chrysin CITCO Clotrimazole Cyclophosphamide Cypermethrin DHEA (prasterone) Efavirenz Ellagic acid Griseofulvin Methoxychlor Mifepristone Nefazodone Nevirapine Nicardipine Octicizer Permethrin Phenobarbital Phenytoin Pregnanedione (5β-dihydroprogesterone) Reserpine TCPOBOP Telmisartan Tolnaftate Troglitazone Valproic acid Antagonists: 3,17β-Estradiol 3α-Androstanol 3α-Androstenol 3β-Androstanol 17-Androstanol AITC Ethinylestradiol Meclizine Nigramide J Okadaic acid PK-11195 S-07662 T-0901317
PXR	Agonists: 17α-Hydroxypregnenolone 17α-Hydroxyprogesterone Δ⁴-Androstenedione Δ⁵-Androstenediol Δ⁵-Androstenedione AA-861 Allopregnanediol Allopregnanedione (5α-dihydroprogesterone) Allopregnanolone (brexanolone) Alpha-Lipoic acid Ambrisentan AMI-193 Amlodipine besylate Antimycotics Artemisinin Aurothioglucose Bile acids Bithionol Bosentan Bumecaine Cafestol Cephaloridine Cephradine Chlorpromazine Ciglitazone Clindamycin Clofenvinfos Chloroxine Clotrimazole Colforsin Corticosterone Cyclophosphamide Cyproterone acetate Demecolcine Dexamethasone DHEA (prasterone) DHEA-S (prasterone sulfate) Dibunate sodium Diclazuril Dicloxacillin Dimercaprol Dinaline Docetaxel Docusate calcium Dodecylbenzenesulfonic acid Dronabinol Droxidopa Eburnamonine Ecopipam Enzacamene Epothilone B Erythromycin Famprofazone Febantel Felodipine Fenbendazole Fentanyl Flucloxacillin Fluorometholone Griseofulvin Guggulsterone Haloprogin Hetacillin potassium Hyperforin Hypericum perforatum (St John's wort) Indinavir sulfate Lasalocid sodium Levothyroxine Linolenic acid LOE-908 Loratadine Lovastatin Meclizine Metacycline Methylprednisolone Metyrapone Mevastatin Mifepristone Nafcillin Nicardipine Nicotine Nifedipine Nilvadipine Nisoldipine Norelgestromin Omeprazole Orlistat Oxatomide Paclitaxel Phenobarbital Piperine Plicamycin Prednisolone Pregnanediol Pregnanedione (5β-dihydroprogesterone) Pregnanolone Pregnenolone Pregnenolone 16α-carbonitrile Proadifen Progesterone Quingestrone Reserpine Reverse triiodothyronine Rifampicin Rifaximin Rimexolone Riodipine Ritonavir Simvastatin Sirolimus Spironolactone Spiroxatrine SR-12813 Suberoylanilide Sulfisoxazole Suramin Tacrolimus Tenylidone Terconazole Testosterone isocaproate Tetracycline Thiamylal sodium Thiothixene Thonzonium bromide Tianeptine Troglitazone Troleandomycin Tropanyl 3,5-dimethulbenzoate Zafirlukast Zeranol Antagonists: Ketoconazole Sesamin
See also Receptor/signaling modulators Nuclear receptor modulators

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