Details of the Drug

General Information of Drug (ID: DM5F84A)

Drug Name
Pipecuronium
Synonyms
Arduan; Pipecurium; Arduan (TN); Piperazinium, 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl); [(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Indication
Disease Entry ICD 11 Status REF
Spasm MB47.3 Approved [1], [2]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 602.9
Topological Polar Surface Area (xlogp) 4.5
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance
The drug present in the plasma can be removed from the body at the rate of 3 mL/min/kg [4]
Elimination
39% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 1.34 - 10.66 (in normal renal function subjects) [4]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.118 micromolar/kg/day [5]
Unbound Fraction
The unbound fraction of drug in plasma is 0.98% [4]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.35 L/kg [4]
Chemical Identifiers
Formula
C35H62N4O4+2
IUPAC Name
[(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-acetyloxy-2,16-bis(4,4-dimethylpiperazin-4-ium-1-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
Canonical SMILES
CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C[C@@H]1N4CC[N+](CC4)(C)C)C)CC[C@]5([C@H]3C[C@@H]([C@@H]5OC(=O)C)N6CC[N+](CC6)(C)C)C
InChI
InChI=1S/C35H62N4O4/c1-24(40)42-32-21-26-9-10-27-28(35(26,4)23-31(32)37-15-19-39(7,8)20-16-37)11-12-34(3)29(27)22-30(33(34)43-25(2)41)36-13-17-38(5,6)18-14-36/h26-33H,9-23H2,1-8H3/q+2/t26-,27+,28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
InChIKey
OWWLUIWOFHMHOQ-XGHATYIMSA-N
Cross-matching ID
PubChem CID
50192
ChEBI ID
CHEBI:8230
CAS Number
68399-58-6
DrugBank ID
DB01338
TTD ID
D0XX6Y

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Neuronal acetylcholine receptor alpha-2 (CHRNA2) TTF4E0J ACHA2_HUMAN Antagonist [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Pipecuronium
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Vecuronium DMP0UK2 Moderate Additive neuromuscular blocking effects by the combination of Pipecuronium and Vecuronium. Tonus and reflex abnormality [MB47] [11]
Coadministration of a Drug Treating the Disease Different from Pipecuronium (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Paromomycin DM1AGXN Major Additive neuromuscular blocking effects by the combination of Pipecuronium and Paromomycin. Amoebiasis [1A36] [12]
Lincomycin DMVTHER Moderate Additive neuromuscular blocking effects by the combination of Pipecuronium and Lincomycin. Gram-positive bacterial infection [1B74-1F40] [13]
Nebivolol DM7F1PA Moderate Additive neuromuscular blocking effects by the combination of Pipecuronium and Nebivolol. Hypertension [BA00-BA04] [14]
Plazomicin DMKMBES Major Additive neuromuscular blocking effects by the combination of Pipecuronium and Plazomicin. Urinary tract infection [GC08] [15]

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 019638.
3 BDDCS applied to over 900 drugs
4 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
6 Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33.
7 Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52.
8 Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity. J Med Chem. 2006 May 4;49(9):2673-6.
9 Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells. Bioorg Med Chem Lett. 2004 Apr 19;14(8):1845-8.
10 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 463).
11 Pandit SK, Ferres CJ, Gibson FM, Mirakhur RK "Time course of action of combinations of vecuronium and pancuronium." Anaesthesia 41 (1986): 151-4. [PMID: 2869710]
12 Burkett L, Bikhazi GB, Thomas KC Jr, Rosenthal DA, Wirta MG, Foldes FF "Mutual potentiation of the neuromuscular effects of antibiotics and relaxants." Anesth Analg 58 (1979): 107-15. [PMID: 571233]
13 Alahdal O, Bevan DR "Clindamycin-induced neuromuscular blockade." Can J Anaesth 42 (1995): 614-7. [PMID: 7553999]
14 Chapple DJ, Clark JS, Hughes R "Interaction between atracurium and drugs used in anaesthesia." Br J Anaesth 55 Suppl 1 (1983): s17-22. [PMID: 6688011]
15 Geha DG, Blitt CD, Moon BJ "Prolonged neuromuscular blockade with pancuronium in the presence of acute renal failure: a case report." Anesth Analg 55 (1976): 343-5. [PMID: 945014]