CAS 101-26-8|pyridostigmine bromide

Introduction：Basic information about CAS 101-26-8|pyridostigmine bromide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. pyridostigmine bromide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles37
7. Synonyms

Common Name	pyridostigmine bromide
CAS Number	101-26-8	Molecular Weight	261.116
Density	0.9613 g/cm3 (20ºC)	Boiling Point	88 (25 torr)
Molecular Formula	C₉H₁₃BrN₂O₂	Melting Point	154 °C
MSDS	ChineseUSA	Flash Point	/
Symbol	GHS06	Signal Word	Danger

Names

Name	Mestinon
Synonym	More Synonyms

pyridostigmine bromide BiologicalActivity

Description	Pyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor.Target: AChEPyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. Since it is a quaternary amine, it is poorly absorbed in the gut and does not cross the blood–brain barrier, except possibly in stressful conditions. Pyridostigmine inhibits acetylcholinesterase in the synaptic cleft, thus slowing down the hydrolysis of acetylcholine. It is a quaternary carbamate inhibitor of cholinesterase that does not cross the blood–brain barrier which carbamylates about 30% of peripheral cholinesterase enzyme. The carbamylated enzyme eventually regenerates by natural hydrolysis and excess ACh levels revert to normal.Pyridostigmine is used to treat muscle weakness in people with myasthenia gravis and to combat the effects of curariform drug toxicity. Pyridostigmine bromide has been FDA approved for military use during combat situations as an agent to be given prior to exposure to the nerve agent Soman in order to increase survival. Used in particular during the first Gulf War, pyridostigmine bromide has been implicated as a causal factor in Gulf War syndrome. Pyridostigmine sometimes is used to treat orthostatic hypotension. It may also be of benefit in chronic axonal polyneuropathy.
Related Catalog	Signaling Pathways >>Neuronal Signaling >>AChEResearch Areas >>Neurological Disease
References	[1]. Gales BJ, et al. Pyridostigmine in the treatment of orthostatic intolerance. Ann Pharmacother. 2007 Feb;41(2):314-8. Epub 2007 Feb 6. [2]. Kanjwal K, et al. Pyridostigmine in the treatment of postural orthostatic tachycardia: a single-center experience. Pacing Clin Electrophysiol. 2011 Jun;34(6):750-5.

Description

Pyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor.Target: AChEPyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. Since it is a quaternary amine, it is poorly absorbed in the gut and does not cross the blood–brain barrier, except possibly in stressful conditions. Pyridostigmine inhibits acetylcholinesterase in the synaptic cleft, thus slowing down the hydrolysis of acetylcholine. It is a quaternary carbamate inhibitor of cholinesterase that does not cross the blood–brain barrier which carbamylates about 30% of peripheral cholinesterase enzyme. The carbamylated enzyme eventually regenerates by natural hydrolysis and excess ACh levels revert to normal.Pyridostigmine is used to treat muscle weakness in people with myasthenia gravis and to combat the effects of curariform drug toxicity. Pyridostigmine bromide has been FDA approved for military use during combat situations as an agent to be given prior to exposure to the nerve agent Soman in order to increase survival. Used in particular during the first Gulf War, pyridostigmine bromide has been implicated as a causal factor in Gulf War syndrome. Pyridostigmine sometimes is used to treat orthostatic hypotension. It may also be of benefit in chronic axonal polyneuropathy.

Related Catalog

Signaling Pathways >>Neuronal Signaling >>AChEResearch Areas >>Neurological Disease

References

[1]. Gales BJ, et al. Pyridostigmine in the treatment of orthostatic intolerance. Ann Pharmacother. 2007 Feb;41(2):314-8. Epub 2007 Feb 6.

[2]. Kanjwal K, et al. Pyridostigmine in the treatment of postural orthostatic tachycardia: a single-center experience. Pacing Clin Electrophysiol. 2011 Jun;34(6):750-5.

Chemical & Physical Properties

Density	0.9613 g/cm3 (20ºC)
Boiling Point	88 (25 torr)
Melting Point	154 °C
Molecular Formula	C₉H₁₃BrN₂O₂
Molecular Weight	261.116
Exact Mass	260.016022
PSA	33.42000
Index of Refraction	1.48 (20ºC)
InChIKey	VNYBTNPBYXSMOO-UHFFFAOYSA-M
SMILES	CN(C)C(=O)Oc1ccc[n+](C)c1.[Br-]
Storage condition	Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UU5270000

CHEMICAL NAME :: Pyridinium, 3-hydroxy-1-methyl-, bromide, dimethylcarbamate (ester)

CAS REGISTRY NUMBER :: 101-26-8

LAST UPDATED :: 199806

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C9-H13-N2-O2.Br

MOLECULAR WEIGHT :: 261.15

WISWESSER LINE NOTATION :: T6KJ A1 COVN1&1 &E

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 7800 ug/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - fasciculations Sense Organs and Special Senses (Eye) - visual field changes Gastrointestinal - nausea or vomiting

REFERENCE :: IJMDAI Israel Journal of Medical Sciences. (POB 1435, Jerusalem 91013, Israel) V.1- 1965- Volume(issue)/page/year: 27,659,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 9 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - fasciculations

REFERENCE :: IJMDAI Israel Journal of Medical Sciences. (POB 1435, Jerusalem 91013, Israel) V.1- 1965- Volume(issue)/page/year: 27,659,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 37500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1042,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2699 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 4,S195,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3100 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 26,145,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2790 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DCTODJ Drug and Chemical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.1- 1977/78- Volume(issue)/page/year: 7,507,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 2,828,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,354,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 ug/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - miosis (pupillary constriction) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: GNRIDX Gendai no Rinsho. (Tokyo, Japan) V.1-10, 1967-76(?). Volume(issue)/page/year: 2,828,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: MECHAN Medicinal Chemistry, A Series of Reviews. (New York, NY) V.1-6, 1951-63. Discontinued. Volume(issue)/page/year: 3,329,1956 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1350 mg/kg/15D-C

TOXIC EFFECTS :: Blood - other changes Musculoskeletal - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

REFERENCE :: TOPADD Toxicologic Pathology. (c/o Dr. F.A. de la Iglesia, Warner-Lambert Co., Pharmaceutical Research Div., POB 1047, Ann Arbor, MI 48106) V.6(3/4)- 1978- Volume(issue)/page/year: 18,387,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 140 mg/kg/14D-I

TOXIC EFFECTS :: Gastrointestinal - ulceration or bleeding from small intestine Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase Related to Chronic Data - death

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 14,40,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 168 mg/kg/28D-I

TOXIC EFFECTS :: Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 14,40,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 540 mg/kg/90D-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

REFERENCE :: FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 14,40,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 225 mg/kg/9W-I

TOXIC EFFECTS :: Blood - other changes Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase

REFERENCE :: JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 48,35,1996 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 630 mg/kg

SEX/DURATION :: female 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 69,291,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 280 mg/kg

SEX/DURATION :: female 15-21 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 69,291,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - physical

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 69,291,1991 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81490 No. of Facilities: 58 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 230 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81490 No. of Facilities: 46 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1619 (estimated) No. of Female Employees: 791 (estimated)

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H300 + H310 + H330-H317
Precautionary Statements	Missing Phrase - N15.00950417-P260-P262-P280-P302 + P352 + P310-P304 + P340 + P310
Personal Protective Equipment	Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes	T+: Very toxic;
Risk Phrases	R26/27/28
Safety Phrases	S22-S36/37/39-S45
RIDADR	UN 2811 6.1/PG 2
RTECS	UU5270000

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Synonyms

3-(Dimethylcarbamoyloxy)-1-methylpyridinium Bromide

Pyridostigminbromid

mestinonbromide

EINECS 202-929-9

ro1-5130

3-Dimethylcarbamoyloxy-1-methyl-pyridinium,Bromid

pyridostigmine

3-dimethylcarbamoyloxy-1-methyl-pyridinium,bromide

MFCD00079283

pyridostigmine bromide

Pyridinium, 3-(((dimethylamino)carbonyl)oxy)-1-methyl-, bromide

regonal

kalymin

Pyridinium, 3-[[(dimethylamino)carbonyl]oxy]-1-methyl-, bromide (1:1)

3-Hydroxy-1

3-((Dimethylcarbamoyl)oxy)-1-methylpyridin-1-ium bromide

mestinonebromide

pyridostygmine bromide

3-[(Dimethylcarbamoyl)oxy]-1-methylpyridinium bromide

3-[[(Dimethylamino)carbonyl]oxy]-1-methylpyridinium Bromide

Pyridostigmine (bromide)

3-{[(dimethylamino)carbonyl]oxy}-1-methylpyridinium bromide

pyridinium, 3-[[(dimethylamino)carbonyl]oxy]-1-methyl-, bromide

kalimin

Mestinon

PYBR

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