Buprenorphine |
![]() Last updated: 06/09/2025 |
![]() |
(Also known as: probuphenine; RX-6029-M) |
|
![]() |
|
An opioid analgesic agent for a variety of animals | |
---|---|---|
|
Used for pain relief or is used as a preanesthetic in a veterinary hospital or clinic setting | |
|
Horses; Hedgehogs; Sheep; Dogs; Cats |
Approval status |
|
Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
---|---|---|
|
Approved |
Chemical structure |
|
Buprenorphine exhibits stereoisomerism, specifically chiral isomerism, due to multiple stereocentres in its complex polycyclic structure. It belongs to the morphinan class of opioids, and its molecular framework includes several fused rings and asymmetric carbon atoms, which give rise to distinct three-dimensional arrangements. The active form of buprenorphine is the (−)-enantiomer, which is responsible for its pharmacological effects as a partial agonist at the μ-opioid receptor and an antagonist at the κ-opioid receptor. This stereoisomer binds with high affinity and slow dissociation, contributing to its long duration of action and reduced risk of respiratory depression compared to full agonists. The stereochemistry is critical: other stereoisomers of buprenorphine do not exhibit the same receptor binding profile or therapeutic efficacy. | |
---|---|---|
|
C₂₉H₄₁NO₄ | |
|
CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O | |
|
C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O | |
|
RMRJXGBAOAMLHD-IHFGGWKQSA-N | |
|
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 | |
|
Yes |
|
![]() |
Common Name | Relationship | Link |
---|---|---|
buprenorphine | - | ![]() |
General status |
|
Analgesic, Medicinal drug | |
---|---|---|
|
Opioid | |
|
- | |
|
- | |
|
Synthetic | |
|
Acts as an epsilon-opioid antagonist | |
|
[Mu-type opioid receptor, partial agonist], [Kappa-type opioid receptor, Antagonist], [Delta-type opioid receptor, Antagonist] | |
|
52485-79-7 | |
|
257-950-6 | |
|
- | |
|
- | |
|
644073 | |
|
Nervous system: Analgesics | |
|
QN02AE01 | |
|
UK: Class C, Schedule 3; EU: UN71, Class IV | |
|
- | |
|
467.65 | |
|
- | |
|
(2S)-2-[(-)-(5R,6R,7R,14S)-9α-cyclopropylmethyl-4,5-epoxy-6,14-ethano-3-hydroxy-6-methoxymorphinan-7-yl]-3,3-dimethylbutan-2-ol | |
|
17-(cyclopropylmethyl)-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-α-methyl-6,14-ethenomorphinan-7-methanol; Buprenex | |
|
- | |
|
- | |
|
- | |
|
White crystalline powder |
Commercial |
|
|
|
|
|
||||||
---|---|---|---|---|---|---|---|---|---|---|
|
Current | |||||||||
|
1965, patented; 1981, first medical approvals | |||||||||
|
Bupaq solution for injection | VetViva Richter GmbH | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | ||||||
Vetergesic, 0.3mg/ml solution for injection for Dog and Cats | Ceva Animal Health Ltd | UK National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
Bupredine multidose solution injection | Le Vet Beheer B.V. | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
Buprevet Multidose Solution for injection | VetViva Richter GmbH | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
|
Formulated as a solution for injection | |||||||||
|
Buprenorphine is produced through a semi-synthetic process starting from thebaine, a naturally occurring alkaloid found in opium. The synthesis involves a Diels–Alder reaction between thebaine and a dienophile to form a key intermediate, which is then alkylated using a Grignard reagent. This is followed by the formation of a cyanamide group, and subsequent deprotection steps to remove protective groups from the cyanamide and phenolic oxygen moieties, typically using alkali or alkaline earth sulphides. The final stages include derivatisation with a cyclopropyl halide and hydrogenation, yielding buprenorphine with its potent opioid receptor activity. | |||||||||
|
Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
|
![]() |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
0.636 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
Low | ||||||||
|
- | - | - | ||||||||
|
209 | L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source |
- | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
9.55 X 1004 | Calculated | - | |||||||
|
4.98 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
High | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
8.31 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) at 25°C3 = Unverified data of known source |
- | ||||||||
- | |||||||||||
|
1.23 X 10-08 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
Low volatility | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- |
Degradation |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
|
- |
Soil adsorption and mobility |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
- | ||||||||||
|
- |
Fate indices |
|
|
|
|
||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||||||||||||||||||||
|
|
- | - | - | |||||||||||||||||||||||||
|
- | - |
Known soil and groundwater metabolites |
None
Other known metabolites |
|
|
|
|
||||
---|---|---|---|---|---|---|---|
norbuprenorphine Note: Pharmacologically active |
- | Human (Liver) | - | ||||
hydroxybuprenorphine | - | Human (Liver) | - | ||||
buprenorphine glucuronide | - | Human (Liver) | - |
|
![]() |
Terrestrial ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
243 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Moderate | ||||||||
|
|
- | - | - | |||||||
|
- | - | |||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
- | |||||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - |
Aquatic ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - |
|
- | - | - | |||
|
- | - | - |
|
![]() |
General |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
High (class III) | - | - | ||||||||
|
243 | Q3 Q = Miscellaneous data from online sources Rat3 = Unverified data of known source |
Moderate | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
Intraperitoneal LD₅₀ = 90 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Mouse3 = Unverified data of known source |
- | ||||||||
Intravenous LD₅₀ = 197 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
- | |||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | |||||||||
|
- | ||||||||||
|
Liver metabolism, excreted ~70 in bile and ~30% in urine | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
- |
Health issues |
|
|
||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
May cuase respiratory depression, decreased blood pressure and heart rate |
Handling issues |
|
|
|||
---|---|---|---|---|
|
No information available | |||
|
Health: H302, H319, H332, H361, H373 | |||
|
Not listed (Not listed) | |||
|
- | |||
|
- | |||
|
- |
|
![]() |
|
|
||
---|---|---|---|
|
buprenorphine | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
buprenorfina | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- |
Record last updated: | 06/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |