4-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-4-(4,4-dimethylpiperazin-4-ium-1-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1,1-dimethylpiperazin-1-ium

• ChemBase ID: 1170
• Molecular Formular: C35H62N4O4++
• Molecular Mass: 602.89118
• Monoisotopic Mass: 602.47710648
• SMILES: O([C@@H]1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4([C@@H](CC3)C[C@H](OC(=O)C)[C@@H](N3CC[N+](CC3)(C)C)C4)C)CC2)C[C@@H]1N1CC[N+](CC1)(C)C)C)C(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H]2CC[C@@H]3[C@@H]([C@]2(C[C@@H]1N1CC[N+](CC1)(C)C)C)CC[C@]1([C@H]3C[C@@H]([C@@H]1OC(=O)C)N1CC[N+](CC1)(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

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-4-(4,4-dimethylpiperazin-4-ium-1-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1,1-dimethylpiperazin-1-ium
• IUPAC Traditional name: 4-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-4-(4,4-dimethylpiperazin-4-ium-1-yl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-13-yl]-1,1-dimethylpiperazin-1-ium
• Brand Name: Raplon
• Synonyms: Pipecurium; Pipecuronium bromide; Pipecuronium

Database IDs

• CAS Number: 68399-58-6
• PubChem SID: 160964633; 46508493
• PubChem CID: 50192

CALCULATED PROPERTIES

JChem

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -5.5202355
• LogD (pH = 7.4): -5.280272
• Log P: -5.2767406
• Molar Refractivity: 193.0382 cm^3
• Polarizability: 68.32886 Å^3
• Polar Surface Area: 59.08 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.41
• LOG S: -6.85
• Solubility (Water): 9.50e-05 g/l

DETAILS

DrugBank - DB01338

• Drug Groups: approved
• Description: Pipecuronium is a piperazinyl androstane derivative which is a non-depolarizing neuromuscular blocking agent.
• Indication: Used as a muscle relaxant during anesthesia and surgical procedures.
• Pharmacology: Pipecuronium is a nondepolarizing neuromuscular blocking agent. Neuromuscular blocking agents produce skeletal muscle paralysis by blocking neural transmission at the myoneural junction. The paralysis is selective initially and usually appears in the following muscles consecutively: levator muscles of eyelids, muscles of mastication, limb muscles, abdominal muscles, muscles of the glottis, and finally, the intercostal muscles and the diaphragm. Neuromuscular blocking agents have no clinically significant effect on consciousness or the pain threshold.
• Affected Organisms: Humans and other mammals
• Half Life: Distribution Normal renal function: 6.22 (range, 1.34 to 10.66) minutes. Renal function impairment: 4.33 (range, 1.69 to 6.17) minutes. Elimination Normal renal function: 1.7 (range, 0.9 to 2.7) hours. The elimination half-life is not altered by hypothermia and bypass. Renal function impairment: 4 (range, 2 to 8.2) hours. [PharmGKB]
• External Links: Wikipedia