1424-27-7

1424-27-7 structure

Name: Acetazolamide
Chemical Name: acetazolamide sodium
CAS Number: 1424-27-7
Molecular Formula: C₄H₅N₄NaO₃S₂
Molecular Weight: 244.22700
Catalog: Signaling Pathways Anti-infection Bacterial
Create Date: 2018-07-17 22:19:51
Modify Date: 2024-01-08 15:01:22
Acetazolamide sodium is the sodium salt of Acetazolamide. Acetazolamide is a carbonic anhydrase (CA) IX inhibitor with an IC50 of 30 nM for hCA IX. Acetazolamide has diuretic, antihypertensive and anti-gonococcal activities[1][4][5][6].

Name	acetazolamide sodium
Synonyms	Sodium acetazolamide Acetazolamide,Monosodium Salt N-(5-Sulfamoyl-1,3,4-thiadiazol-2-yl)acetamide monosodium salt Acetazolamide sodium sodium,(5-acetamido-1,3,4-thiadiazol-2-yl)sulfonylazanide ACETAMIDE,N-(5-SULFAMOYL-1,3,4-THIADIAZOL-2-YL)-,MONOSODIUM SALT Acetamide,N-(5-(aminosulfonyl)-1,3,4-thiadiazol-2-yl)-,monosodium salt Acetazolamide sodium salt UNII-429ZT169UH

Description	Acetazolamide sodium is the sodium salt of Acetazolamide. Acetazolamide is a carbonic anhydrase (CA) IX inhibitor with an IC50 of 30 nM for hCA IX. Acetazolamide has diuretic, antihypertensive and anti-gonococcal activities[1][4][5][6].
Related Catalog	Research Areas >> Infection Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Metabolic Enzyme/Protease >> Carbonic Anhydrase Research Areas >> Metabolic Disease Signaling Pathways >> Anti-infection >> Bacterial
In Vitro	Acetazolamide also inhibits hCA II with an IC50 of 130 nM[1]. Acetazolamide (Ace) is a small heteroaromatic sulfonamide that binds to various carbonic anhydrases with high affinity, acting as a carbonic anhydrase (CA) inhibitor[2]. Compared with the control group, the high Acetazolamide concentration (AceH, 50 nM), Cisplatin (Cis; 1 µg/mL) and Cis combined with the low Acetazolamide concentration (AceL, 10 nM) treatments significantly reduces viability of Hep-2 cells[2]. Treatment with the Acetazolamide/Cis combination significantly increases the expression levels of P53, as both AceL+Cis and AceH+Cis treatments result in significantly increased P53 protein expression levels compared with the control group. The Ace/Cis combination treatment significantly reduces the bcl-2/bax expression ratio, and increases the expression of caspase-3 protein, compared with the control group. AceL, AceH, Cis and AceL+Cis treatments significantly reduce the bcl-2/bax ratio compared with the control group[2]. Combined Ace and Cis treatment effectively promotes apoptosis in Hep-2 cells[2]. Combined treatment with Ace/Cis markedly decreases the expression of AQP1 mRNA in Hep-2 cells. Both AceH and AceL+Cis treatments decrease the expression of aquaporin-1 (AQP1) mRNA in Hep-2 cells compared with the control group[2].
In Vivo	Acetazolamide (40 mg/kg) significantly potentiates the inhibitory effect of MS-275 on tumorigenesis in neuroblastoma (NB) SH-SY5Y xenografts[3]. Acetazolamide (40 mg/kg) and/or MS-275 treatment reduce expression of HIF1-α and CAIX in NB SH-SY5Y xenograft[3]. Acetazolamide (40 mg/kg), MS-275 and Acetazolamide+MS-275 reduce expression of mitotic and proliferative markers in NB SH-SY5Y xenografts[3].Acetazolamide (50 mg/kg; PO, for 3 days) significantly reduces the gonococcal load in the vagina of infected mice by 90%[6].
References	[1]. Bayat Mokhtari R, et al. Acetazolamide potentiates the anti-tumor potential of HDACi, MS-275, in neuroblastoma. BMC Cancer. 2017 Feb 24;17(1):156. [2]. Hou Z, et al. Dual-tail approach to discovery of novel carbonic anhydrase IX inhibitors by simultaneously matching the hydrophobic and hydrophilic halves of the active site. Eur J Med Chem. 2017 May 26;132:1-10. [3]. Gao H, et al. Combined treatment with acetazolamide and cisplatin enhances chemosensitivity in laryngeal carcinoma Hep-2 cells. Oncol Lett. 2018 Jun;15(6):9299-9306. [4]. Kassamali R, et al. Acetazolamide: a forgotten diuretic agent. Cardiol Rev. 2011 Nov-Dec;19(6):276-8. [5]. Jabeen E, et al. Interaction of antihypertensive acetazolamide with nonsteroidal anti-inflammatory drugs. J Photochem Photobiol B. 2013 Aug 5;125:155-63. [6]. Abutaleb NS, et al. In vivo efficacy of acetazolamide in a mouse model of Neisseria gonorrhoeae infection. Microb Pathog. 2022 Mar;164:105454.

Melting Point	258-259ºC (EFFERVESCENCE)
Molecular Formula	C₄H₅N₄NaO₃S₂
Molecular Weight	244.22700
Exact Mass	243.97000
PSA	142.87000
LogP	0.78380

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC8400000

CHEMICAL NAME :: Acetamide, N-(5-sulfamoyl-1,3,4-thiadiazol-2-yl)-, monosodium salt

CAS REGISTRY NUMBER :: 1424-27-7

LAST UPDATED :: 199609

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C4-H5-N4-O3-S2.Na

MOLECULAR WEIGHT :: 244.24

WISWESSER LINE NOTATION :: T5NN DSJ CSZW EMV1 &-NA-

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1 gm/kg

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

REFERENCE :: JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3 gm/kg

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

REFERENCE :: JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 gm/kg

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

REFERENCE :: JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 1500 mg/kg

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

REFERENCE :: JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1 gm/kg/10D-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - changes in sodium Nutritional and Gross Metabolic - changes in potassium

REFERENCE :: JHHBAI Bulletin of the Johns Hopkins Hospital. (Baltimore, MD) V.1-119, 1889-1966. For publisher information, see JHMJAX. Volume(issue)/page/year: 95,199,1954 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1 gm/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 1,51,1968

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1 gm/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 1,51,1968

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 850 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,355,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1 gm/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 10,221,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 200 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 27,51,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1 gm/kg

SEX/DURATION :: female 8 day(s) after conception

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

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,45,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 3 gm/kg

SEX/DURATION :: female 9-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,45,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 200 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 28,45,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1500 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - cytological changes (including somatic cell genetic material)

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 15,199,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 1500 mg/kg

SEX/DURATION :: female 13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 15,199,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 300 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 4,95,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 600 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 4,95,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravaginal

DOSE :: 110 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 7,209,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5616 No. of Facilities: 17 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 223 (estimated) No. of Female Employees: 137 (estimated)

Hazard Codes	Xi

59-66-5	1189904-01-5
1424-27-7	98-75-9
32873-56-6	2349-67-9
60320-32-3	5393-55-5
80495-47-2	120208-98-2