General
Preferred name
TAPENTADOL
Synonyms
TAPENTADOL HYDROCHLORIDE ()
Nucynta Er ()
CG5503 HYDROCHLORIDE ()
Nucynta ()
BN-200 HYDROCHLORIDE ()
CG-5503 HYDROCHLORIDE ()
Palexia ()
Tapentadol hcl ()
CG5503 IR ()
CG5503 (BASE) ()
NSC-759619 ()
BN-200 ()
CG5503 ()
BN 200 (BASE) ()
CG-5503 ()
Tapentadol (hydrochloride) ()
Tapentadol (hydrochloride) (CRM) ()
Tapentadol-d3 (hydrochloride) (CRM) ()
P&D ID
PD009322
CAS
175591-09-0
175591-23-8
1435782-38-9
Tags
available
drug
Approved by
FDA
First approval
2008
Drug Status
approved
Drug indication
Acute pain
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ABSORPTION Bioavailability, immediate release (IR), 86 mg: 32%; ; Bioavailability, extended release (ER), 86 mg: 32%; ; Cmax, IR: 64.2 ng/mL;; Cmax, ER: 22.5 ng/mL; ; T max, IR: 1.5 hours;; T max, ER: 5.0 hours;; Tapentadol accumulates following multiple repeat doses. ; ;
PHARMACODYNAMICS Tapentadol is a centrally-acting synthetic analgesic that is 18 times less potent than morphine in binding mu-opioid receptors. It also increases norepinephrine concentrations in the brains of rats via inhibition of norepinephrine reuptake. Selective mu-opioid antagonists like naloxone can block analgesia from tapentadol. It also has not effect on the QT interval.
MOA Tapendadol causes large increases in levels of extracellular norepinephrine (NE) due to a dual mechanism of action involving mu opioid receptor (MOR) agonism as well as noradrenaline reuptake inhibition.; ;
TOXICITY Oral, rabbit: LD50 = 3200 mg/kg;; Oral, mouse: LD50 = 300 mg/kg;; Oral, rat: LD50: 980 mg/kg;; The most common reasons for discontinuation due to adverse events were dizziness, nausea, vomiting, somnolence, and headache.
DESCRIPTION The marketed formulation contains tapentadol hydrochloride (PubChem CID 9838021). (GtoPdb)
Compound Sets
17
Cayman Chemical Bioactives
18730
18660
9000620
ChEMBL Approved Drugs
CHEMBL1201777
CHEMBL1201776
ChEMBL Drugs
CHEMBL1201777
CHEMBL1201776
Concise Guide to Pharmacology 2017/18
7477
Concise Guide to Pharmacology 2019/20
7477
Concise Guide to Pharmacology 2021/22
7477
Concise Guide to Pharmacology 2023/24
7477
DrugBank
DB06204
DrugBank Approved Drugs
DB06204
DrugCentral
4283
DrugCentral Approved Drugs
4283
DrugMAP
DMXLSH3
DrugMAP Approved Drugs
DMXLSH3
Guide to Pharmacology
7477
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1201776
NCATS Inxight Approved Drugs
H8A007M585
ReFrame library
External IDs
54
Properties
(calculated by RDKit )
Molecular Weight
221.18
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
5
Ring Count
1
Aromatic Ring Count
1
cLogP
3.08
TPSA
23.47
Fraction CSP3
0.57
Chiral centers
2.0
Largest ring
6.0
QED
0.83
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Source data