4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide

Modify Date: 2025-08-25 13:39:53

4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide Structure
4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide structure
 Common Name 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide
CAS Number 52212-02-9 Molecular Weight 762.69900
Density 1.329 Boiling Point N/A
Molecular Formula C35H62Br2N4O4 Melting Point 262-264ºC
MSDS N/A Flash Point N/A

 Use of 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide


Pipecuronium bromide is a potent long-acting nondepolarizing steroidal neuromuscular blocking agent (NMBA), and a bisquaternary ammonium compound. Pipecuronium bromide is a powerful competitive nAChR antagonist with a Kd of 3.06 μM[1][2][3][4][5].

 Names

Name 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide
Synonym More Synonyms

  Biological Activity

Description Pipecuronium bromide is a potent long-acting nondepolarizing steroidal neuromuscular blocking agent (NMBA), and a bisquaternary ammonium compound. Pipecuronium bromide is a powerful competitive nAChR antagonist with a Kd of 3.06 μM[1][2][3][4][5].
Related Catalog
Target

nAChR[4][5]

In Vitro Sugammadex has a high affinity for Pipecuronium bromide. As Pipecuronium bromide is about 6 to 7 times more potent than Rocuronium, fewer molecules are required to achieve a comparative blockade than in the case of Rocuronium[1].
In Vivo The average ED95 is 0.045mg/kg (0.035-0.059 mg/kg) of Pipecuronium bromide, the onset of action varies between 2 and 6.3 minutes, depending on the dose and the background anesthesia. Pipecuronium bromide does not liberate histamine, it has no cardiovascular side effects even in doses of 3× ED95, and anaphylaxis does not appear to be a problem[2]. Carboxymethylated γ-cyclodextrin shows efficient and complete reversal of the Pipecuronium bromide induced neuromuscular block in an ex vivo rat diaphragm experiment[3].
References

[1]. Tassonyi E, et al. Reversal of Pipecuronium-Induced Moderate Neuromuscular Block with Sugammadex in the Presence of a Sevoflurane Anesthetic: A Randomized Trial. Anesth Analg. 2015 Aug;121(2):373-80.

[2]. Tassonyi E, et al. Reversal of Deep Pipecuronium-Induced Neuromuscular Block With Moderate Versus Standard Dose of Sugammadex: A Randomized, Double-Blind, Noninferiority Trial. Anesth Analg. 2018 Dec;127(6):1344-1350.

[3]. Alánt O, et al. First clinical experience with a new neuromuscular blocker pipecurium bromide. Arzneimittelforschung. 1980;30(2a):374-9.

[4]. Töröcsik A, et al. Characterization of somatodendritic neuronal nicotinic receptors located on the myenteric plexus. Eur J Pharmacol. 1991 Sep 24;202(3):297-302.

[5]. Kárpáti E, et al. Investigation of neuromuscular blocking agents at Richter Ltd. Acta Pharm Hung. 2002;72(1):37-48.

 Chemical & Physical Properties

Density 1.329
Melting Point 262-264ºC
Molecular Formula C35H62Br2N4O4
Molecular Weight 762.69900
Exact Mass 760.31400
PSA 59.08000
InChIKey FMUOAYRSFAPXFH-MHLFSCIFSA-M
SMILES CC(=O)OC1CC2CCC3C(CCC4(C)C3CC(N3CC[N+](C)(C)CC3)C4OC(C)=O)C2(C)CC1N1CC[N+](C)(C)CC1.[Br-]

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TM3170000
CHEMICAL NAME :
Piperazinium, 4,4'-(3,17-dihydroxyandrostan-2,16-diyl)bis(1,1-dimet hyl-, dibromide, diacetate
CAS REGISTRY NUMBER :
52212-02-9
LAST UPDATED :
199012
DATA ITEMS CITED :
9
MOLECULAR FORMULA :
C35-H62-N4-O4.2Br
MOLECULAR WEIGHT :
762.83
WISWESSER LINE NOTATION :
L E5 B666TJ A1 E1 FOV1 OOV1 G- DT6K DNTJ A1 A1& P- DT6K DNTJ A1 A1 &E 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
450 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
456 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
173 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
70600 ng/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
60500 ng/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
29700 ng/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
55300 ng/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
10200 ng/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,346,1980

 Safety Information

Hazard Codes Xi
Risk Phrases R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Phrases S26-S36
WGK Germany 3
RTECS GN6820000
HS Code 29322980

 Synthetic Route

Methyl bromide structure

Methyl bromide

CAS#:74-83-9

N/A structure

N/A

CAS#:52211-99-1

~92%

4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide Structure

4,4'-((2beta,3a...

CAS#:52212-02-9

Literature: Tuba Arzneimittel-Forschung/Drug Research, 1980 , vol. 30, # 2 A p. 342 - 346

 Precursor & DownStream

Precursor  1

DownStream  0

 Customs

HS Code 29322980

 Synonyms

PIPECURINIUM BROMIDE
PIPECURIUM BROMIDE
Ardtm
Pipecuronium
RGH-1106
EINECS 257-740-4
Arduan (tn)
pipecuronium bromide
Pipecuroniumbromid
Pipecuriurn Brmnide
Arduan
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Chemsrc provides CAS#:52212-02-9 MSDS, density, melting point, boiling point, structure, etc. Its name is 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide>> amp version: 4,4'-((2beta,3alpha,5alpha,16beta,17beta)-3,17-Bis(acetyloxy)androstane-2,16-diyl)bis(1,1-dimethyl-piperazinium) dibromide

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