(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol

• ChemBase ID: 797
• Molecular Formular: C29H41NO4
• Molecular Mass: 467.64014
• Monoisotopic Mass: 467.3035588
• SMILES: O1[C@@H]2[C@]34[C@]5(C[C@@H]([C@]2(OC)CC5)C(O)(C(C)(C)C)C)[C@H](N(CC3)CC2CC2)Cc2c4c1c(O)cc2
• Canonical SMILES: CO[C@]12CC[C@]3(C[C@@H]1C(C(C)(C)C)(O)C)[C@@]14[C@H]2Oc2c4c(C[C@H]3N(CC1)CC1CC1)ccc2O
• InChI: InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1
• InChIKey: RMRJXGBAOAMLHD-IHFGGWKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7,9,11-trien-11-ol
• IUPAC Traditional name: buprenorphine hydrochloride
• Brand Name: Buprenex; Subutex; Temgesic; Buprel; Probuphine
• Synonyms: Buprenorfina [INN-Spanish]; Buprenophine; Buprenorphine Hcl; Buprenorphinum [INN-Latin]; buprenorphine; Buprenorphine

Database IDs

• CAS Number: 52485-79-7
• PubChem SID: 160964260; 46505782
• PubChem CID: 644073; 40400

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.415402
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.58735055
• LogD (pH = 7.4): 1.6101108
• Log P: 3.5498807
• Molar Refractivity: 131.7623 cm^3
• Polarizability: 52.271748 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.53
• LOG S: -4.44
• Solubility (Water): 1.68e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.8

DETAILS

DrugBank - DB00921

• Drug Groups: illicit; approved; investigational
• Description: A derivative of the opioid alkaloid thebaine that is a more potent and longer lasting analgesic than morphine. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use. [PubChem]
• Indication: For the treatment of moderate to severe pain, peri-operative analgesia, and opioid dependence.
• Pharmacology: Buprenorphine is a synthetic opioid analgesic and thebaine derivative, with a longer duration of action than morphine. Buprenorphine interacts predominately with the opioid mu-receptor. These mu-binding sites are discretely distributed in the human brain, spinal cord, and other tissues. In clinical settings, buprenorphine exerts its principal pharmacologic effects on the central nervous system. Its primary actions of therapeutic value are analgesia and sedation. Buprenorphine may increase the patient's tolerance for pain and decrease the perception of suffering, although the presence of the pain itself may still be recognized. In addition to analgesia, alterations in mood, euphoria and dysphoria, and drowsiness commonly occur. Buprenorphine depresses the respiratory centers, depresses the cough reflex, and constricts the pupils.
• Toxicity: Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Buprenorphine undergoes both N-dealkylation to norbuprenorphine and glucuronidation. The N-dealkylation pathway is mediated by cytochrome P-450 3A4 isozyme. Norbuprenorphine, an active metabolite, can further undergo glucuronidation.
• Absorption: 31% bioavailability (sublingual)
• Half Life: 37 hours
• Protein Binding: 96%
• Elimination: Buprenorphine, in common with morphine and other phenolic opioid analgesics, is metabolized by the liver and its clearance is related to hepatic blood flow.
• References: Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. [Pubmed] ; Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Huang P, Kehner GB, Cowan A, Liu-Chen LY: Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist. J Pharmacol Exp Ther. 2001 May;297(2):688-95. Pubmed
• Bodkin JA, Zornberg GL, Lukas SE, Cole JO: Buprenorphine treatment of refractory depression. J Clin Psychopharmacol. 1995 Feb;15(1):49-57. Pubmed