beta-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-b)pyran-6-yl ester, hydrochloride (1:1)
Basic information
- CAS
138605-00-2- Standard SMILES
C=C[C@@]1(C)CC(=O)[C@]2(O)[C@@]3(C)[C@@H](O)CCC(C)(C)[C@@H]3[C@H](OC(=O)CCN(C)C)[C@H](OC(C)=O)[C@@]2(C)O1.Cl- InChIKey
VIRRLEDAYYYTOD-YHEOSNBFSA-N- Molecular formula
- C27H44ClNO8
- Average molar mass
- 546.1 g/mol
- Monoisotopic mass
- 545.2755451
Overview
Colforsin daropate hydrochloride is the hydrochloride salt of colforsin daropate. It is a drug used for the treatment of acute heart failure. It directly stimulates adenylate cyclase and produces positive inotropic and vasodilator effects accompanied by the increase in cellular cAMP. It has a role as a vasodilator agent, an antihypertensive agent, a cardiotonic drug and an adenylate cyclase agonist. It contains a colforsin daropate(1+).
Names & identifiers
- Preferred name
- beta-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-b)pyran-6-yl ester, hydrochloride (1:1)
- IUPAC
- [(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-(dimethylamino)propanoate;hydrochloride
- English name
- N,N-Dimethyl-(3R,4aR,5S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyldodecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho[2,1-b]pyran-6-yl ester β-alanine hydrochloride
- Molecular formula
- C27H44ClNO8
- Molecular weight
- 546.1
Names & synonyms
138605-00-2AdehlColforsin daropate hydrochlorideColforsin dapropate hydrochlorideColforsin dapropate HCl6-(3-Dimethylaminopropionyl)forskolin hydrochlorideC6P4R272GTCHEBI:31429RefChem:578509BETA-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-B)PYRAN-6-YL ESTER, HYDROCHLORIDE (1:1)NKH-477colforsin daropate HCl
Show more names
MKH 477NKH 477Forskolin, NKH477Colforsin dapropateVIRRLEDAYYYTOD-YHEOSNBFSA-Ncolforsindapropatehydrochloride
NKH477 (hydrochloride)beta-Alanine, N,N-dimethyl-, (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(acetyloxy)-3-ethenyldecahydro-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-1H-naphtho(2,1-b)pyran-6-yl ester, hydrochlorideColforsin daropate hydrochloride (JAN)[(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-(dimethylamino)propanoate;hydrochlorideAdehl (TN)Colforsin daropate hciCOLFORSIN DAROPATE HYDROCHLORIDE [JAN]UNII-C6P4R272GT
Properties
Computed structural properties
- Topological polar surface area
- 123 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 8
- Heavy atoms
- 37
- Formal charge
- 0
- Complexity
- 933
Physicochemical properties
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O: · H2O: soluble3mg/mL, clear to slightly hazy (warmed)
- form
- White solid
- color
- white to beige
- Water Solubility
- 40 mM · Soluble to 40 mM in water
- InChIKey
- VIRRLEDAYYYTOD-YHEOSNBFSA-N
- SMILES
- Cl.CN(C)CCC(=O)O[C@@H]1[C@H](OC(C)=O)[C@@]2(C)O[C@](C)(CC(=O)[C@]2(O)[C@@]3(C)[C@@H](O)CCC(C)(C)[C@H]13)C=C
- FDA UNII
- 6 P4R272GT · C6P4R272GT
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 300 · H300
- Precautionary statements
- 264 · P264-P270-P301+P310-P405-P501
- Hazard Codes
- T+
- Risk Statements
- 28 · 28
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 1 (100%)
Safety data
- wgk
- 3
- rtecs
- AY5992600
- ridadr
- UN 2811 6.1 / PGII
- risk_code
- 28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 28-36/37-45
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard statements
- H300
- Hazard Classifications
- Acute Tox. 2 Oral
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Applications
DescriptionColforsin daropate was launched in Japan as a treatment for acute heart failure. It is a water-soluble and orally active 3-dimethylaminopropionyl (daropate) derivative of forskolin, a labdane-type diterpene isolated from the root of Coleus forskohlii. It is obtained from forskolin in 7 steps based upon a series of protections and deprotections of the different OH groups and a key 7,8- transacylation. Colforsin daropate is the first in its class of adenylate cyclase activators to be marketed in the treatment of heart failure. As forskolin, it directly stimulates adenylate cyclase thus increasing intracellular concentration of cAMP and inhibiting calcium mobilization. As a direct consequence, it induces a significant vasodilatation, so provides a moderate positive inotropic and chronotropic effect. In contrast with well-established generators of cAMP synthesis (dobutamine), Colforsin daropate maintains its action on cardiac muscle in the severe stage even when the beta-adrenoceptor is down-regulated in myocardium. In several clinical trials in patients with severe congestive heart failure (CHF), Colforsin daproate improved hemodynamic symptoms of heart failure patients without serious adverse effects.
UsesNKH 477 is a water-soluble analog of Forskolin (F701800), that is a potent activator of adenylyl cyclase, which shows some selectivity for cardiac (type V) adenylyl cyclase).
Additional notes
DefinitionChEBI: Colforsin daropate hydrochloride is the hydrochloride salt of colforsin daropate. It is a drug used for the treatment of acute heart failure. It directly stimulates adenylate cyclase and produces positive inotropic and vasodilator effects accompanied by the increase in cellular cAMP. It has a role as an adenylate cyclase agonist, an antihypertensive agent, a cardiotonic drug and a vasodilator agent. It contains a colforsin daropate(1+).
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