Identification
- Generic Name
- Colforsin
- DrugBank Accession Number
- DB02587
- Background
Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant Coleus forskohlii. Has antihypertensive, positive inotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Colforsin (DB02587)
- Weight
- Average: 410.5012
Monoisotopic: 410.230453442 - Chemical Formula
- C22H34O7
- Synonyms
- 7β-acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one
- Coleonolk
- Colforsin
- colforsina
- colforsine
- colforsinum
- Forskolin
- External IDs
- 266-410-9
- HL-362
- L-75-1362B
- NSC-357088
- NSC-375489
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAdenylate cyclase type 2 Not Available Humans UGuanine nucleotide-binding protein G(s) subunit alpha isoforms short Not Available Humans UAdenylate cyclase type 5 Not Available Humans UCystic fibrosis transmembrane conductance regulator inhibitorHumans AAdenylate cyclase activatorHumans UCalcium-activated potassium channel activatorHumans UCREB-binding protein activatorHumans UExtracellular signal-regulated kinase (ERK) activatorHumans UMucin-2 activatorHumans UPlasminogen activator inhibitor 1 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareIloprost Iloprost may increase the hypotensive activities of Colforsin. Isosorbide mononitrate Colforsin may increase the vasodilatory activities of Isosorbide mononitrate. Patent Blue The therapeutic efficacy of Colforsin can be decreased when used in combination with Patent Blue. - Food Interactions
- Not Available
Categories
- Drug Categories
- Adjuvants, Immunologic
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Cardiotonic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Diterpenes
- Immunologic Factors
- P-glycoprotein inhibitors
- Peripheral Nervous System Agents
- Protective Agents
- Respiratory System Agents
- Terpenes
- Vasodilating Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Triterpenoids
- Direct Parent
- Triterpenoids
- Alternative Parents
- Naphthopyrans / Naphthalenes / Pyrans / Oxanes / Tertiary alcohols / Secondary alcohols / Ketones / Cyclic alcohols and derivatives / Carboxylic acid esters / Polyols show 5 more
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic alcohol / Dialkyl ether / Ether / Hydrocarbon derivative / Ketone show 15 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cyclic ketone, organic heterotricyclic compound, acetate ester, triol, labdane diterpenoid (CHEBI:42471) / Labdane and halimane diterpenoids, Diterpenoids (C20) (C09076) / Labdane and halimane diterpenoids (LMPR0104030004)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1F7A44V6OU
- CAS number
- 66575-29-9
- InChI Key
- OHCQJHSOBUTRHG-KGGHGJDLSA-N
- InChI
- InChI=1S/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16-,17-,19-,20-,21+,22-/m0/s1
- IUPAC Name
- (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
- SMILES
- [H][C@]1(O)CCC(C)(C)[C@]2([H])[C@]([H])(O)[C@]([H])(OC(C)=O)[C@@]3(C)O[C@](C)(CC(=O)[C@]3(O)[C@@]12C)C=C
References
- Synthesis Reference
Emiko Yamasaki, Takaaki Ohkuma, "Lyophilized preparation of 6-(3-dimethylaminopropionyl)forskolin." U.S. Patent US5051132, issued June, 1974.
US5051132- General References
- Not Available
- External Links
- KEGG Drug
- D03584
- KEGG Compound
- C09076
- PubChem Compound
- 47936
- PubChem Substance
- 46509044
- ChemSpider
- 43607
- BindingDB
- 50010261
- ChEBI
- 42471
- ChEMBL
- CHEMBL52606
- ZINC
- ZINC000003977779
- PharmGKB
- PA146096022
- PDBe Ligand
- FOK
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Forskolin
- PDB Entries
- 1ab8 / 1cjk / 1cjt / 1cju / 1cjv / 1cs4 / 1cul / 1tl7 / 1u0h / 3c14 … show 6 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.1 mg/mL ALOGPS logP 1.28 ALOGPS logP 1.36 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 11.57 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 113.29 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 104.47 m3·mol-1 Chemaxon Polarizability 43.32 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.6195 Blood Brain Barrier + 0.6888 Caco-2 permeable - 0.6796 P-glycoprotein substrate Substrate 0.8361 P-glycoprotein inhibitor I Inhibitor 0.8198 P-glycoprotein inhibitor II Inhibitor 0.6788 Renal organic cation transporter Non-inhibitor 0.8998 CYP450 2C9 substrate Non-substrate 0.7961 CYP450 2D6 substrate Non-substrate 0.892 CYP450 3A4 substrate Substrate 0.7016 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.935 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Inhibitor 0.7959 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9606 Ames test Non AMES toxic 0.6284 Carcinogenicity Non-carcinogens 0.9539 Biodegradation Not ready biodegradable 0.9792 Rat acute toxicity 2.2384 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9911 hERG inhibition (predictor II) Non-inhibitor 0.8782
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.1379792 predictedDarkChem Lite v0.1.0 [M-H]- 201.0616856 predictedDarkChem Lite v0.1.0 [M-H]- 201.4859856 predictedDarkChem Lite v0.1.0 [M-H]- 187.53746 predictedDeepCCS 1.0 (2019) [M+H]+ 184.7026493 predictedDarkChem Lite v0.1.0 [M+H]+ 201.2570856 predictedDarkChem Lite v0.1.0 [M+H]+ 202.0044856 predictedDarkChem Lite v0.1.0 [M+H]+ 189.36235 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.6757073 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.7668856 predictedDarkChem Lite v0.1.0 [M+Na]+ 195.2349 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein heterodimerization activity
- Specific Function
- Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:15385642). Down-stream signaling cascades mediate changes in gene expression patterns and lead to i...
- Gene Name
- ADCY2
- Uniprot ID
- Q08462
- Uniprot Name
- Adenylate cyclase type 2
- Molecular Weight
- 123602.25 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Signal transducer activity
- Specific Function
- Guanine nucleotide-binding proteins (G proteins) function as transducers in numerous signaling pathways controlled by G protein-coupled receptors (GPCRs) (PubMed:17110384). Signaling involves the a...
- Gene Name
- GNAS
- Uniprot ID
- P63092
- Uniprot Name
- Guanine nucleotide-binding protein G(s) subunit alpha isoforms short
- Molecular Weight
- 45664.205 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein heterodimerization activity
- Specific Function
- Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling (PubMed:15385642, PubMed:26206488, PubMed:24700542). Mediates signaling downstream of ADRB1 (PubMed:2470054...
- Gene Name
- ADCY5
- Uniprot ID
- O95622
- Uniprot Name
- Adenylate cyclase type 5
- Molecular Weight
- 138906.37 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Pdz domain binding
- Specific Function
- Involved in the transport of chloride ions. May regulate bicarbonate secretion and salvage in epithelial cells by regulating the SLC4A7 transporter. Can inhibit the chloride channel activity of ANO...
- Gene Name
- CFTR
- Uniprot ID
- P13569
- Uniprot Name
- Cystic fibrosis transmembrane conductance regulator
- Molecular Weight
- 168139.895 Da
References
- Ramesh Babu PB, Chidekel A, Utidjian L, Shaffer TH: Regulation of apical surface fluid and protein secretion in human airway epithelial cell line Calu-3. Biochem Biophys Res Commun. 2004 Jul 9;319(4):1132-7. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Activator
- General Function
- Metal ion binding
- Specific Function
- Catalyzes the formation of the signaling molecule cAMP in response to G-protein signaling. Mediates responses to increased cellular Ca(2+)/calmodulin levels (By similarity). May be involved in regu...
Components:
References
- Uckert S, Stief CG, Lietz B, Burmester M, Jonas U, Machtens SA: Possible role of bioactive peptides in the regulation of human detrusor smooth muscle - functional effects in vitro and immunohistochemical presence. World J Urol. 2002 Sep;20(4):244-9. doi: 10.1007/s00345-002-0287-y. Epub 2002 Jul 23. [Article]
- Al-Hazza A, Linley J, Aziz Q, Hunter M, Sandle G: Upregulation of basolateral small conductance potassium channels (KCNQ1/KCNE3) in ulcerative colitis. Biochem Biophys Res Commun. 2016 Feb 5;470(2):473-478. doi: 10.1016/j.bbrc.2015.12.086. Epub 2015 Dec 21. [Article]
- Lando M, Abemayor E, Verity MA, Sidell N: Modulation of intracellular cyclic adenosine monophosphate levels and the differentiation response of human neuroblastoma cells. Cancer Res. 1990 Feb 1;50(3):722-7. [Article]
- Aiyar N, Disa J, Dang K, Pronin AN, Benovic JL, Nambi P: Involvement of G protein-coupled receptor kinase-6 in desensitization of CGRP receptors. Eur J Pharmacol. 2000 Sep 1;403(1-2):1-7. doi: 10.1016/s0014-2999(00)00419-2. [Article]
- Monaghan TK, Mackenzie CJ, Plevin R, Lutz EM: PACAP-38 induces neuronal differentiation of human SH-SY5Y neuroblastoma cells via cAMP-mediated activation of ERK and p38 MAP kinases. J Neurochem. 2008 Jan;104(1):74-88. doi: 10.1111/j.1471-4159.2007.05018.x. Epub 2007 Nov 6. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Voltage-gated potassium channel activity
- Specific Function
- Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activati...
Components:
References
- Hamada Y, Nakaya Y, Hamada S, Kamada M, Aono T: Activation of K+ channels by ritodrine hydrochloride in uterine smooth muscle cells from pregnant women. Eur J Pharmacol. 1994 Dec 15;288(1):45-51. doi: 10.1016/0922-4106(94)90008-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Acetylates histones, giving a specific tag for transcriptional activation. Also acetylates non-histone proteins, like NCOA3 and FOXO1. Binds specifically to phosphorylated CREB and enhances its tra...
- Gene Name
- CREBBP
- Uniprot ID
- Q92793
- Uniprot Name
- CREB-binding protein
- Molecular Weight
- 265349.765 Da
References
- Hansen TV, Rehfeld JF, Nielsen FC: KCl and forskolin synergistically up-regulate cholecystokinin gene expression via coordinate activation of CREB and the co-activator CBP. J Neurochem. 2004 Apr;89(1):15-23. doi: 10.1046/j.1471-4159.2003.02252.x. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Rna polymerase ii carboxy-terminal domain kinase activity
- Specific Function
- Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK ca...
Components:
References
- Monaghan TK, Mackenzie CJ, Plevin R, Lutz EM: PACAP-38 induces neuronal differentiation of human SH-SY5Y neuroblastoma cells via cAMP-mediated activation of ERK and p38 MAP kinases. J Neurochem. 2008 Jan;104(1):74-88. doi: 10.1111/j.1471-4159.2007.05018.x. Epub 2007 Nov 6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Not Available
- Specific Function
- Coats the epithelia of the intestines, airways, and other mucus membrane-containing organs. Thought to provide a protective, lubricating barrier against particles and infectious agents at mucosal s...
- Gene Name
- MUC2
- Uniprot ID
- Q02817
- Uniprot Name
- Mucin-2
- Molecular Weight
- 540296.38 Da
References
- Heerdt BG, Houston MA, Rediske JJ, Augenlicht LH: Steady-state levels of mitochondrial messenger RNA species characterize a predominant pathway culminating in apoptosis and shedding of HT29 human colonic carcinoma cells. Cell Growth Differ. 1996 Jan;7(1):101-06. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Serine-type endopeptidase inhibitor activity
- Specific Function
- Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major con...
- Gene Name
- SERPINE1
- Uniprot ID
- P05121
- Uniprot Name
- Plasminogen activator inhibitor 1
- Molecular Weight
- 45059.695 Da
References
- Nonaka T, Matsumoto H, Shimada W, Miyagi I, Okada K, Fukao H, Ueshima S, Kikuchi H, Tanaka S, Matsuo O: Effect of cyclic AMP on urokinase-type plasminogen activator receptor and fibrinolytic factors in a human osteoblast-like cell line. Biochim Biophys Acta. 1995 Apr 6;1266(1):50-6. doi: 10.1016/0167-4889(94)00220-9. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 27, 2022 16:54