Nitrofurantoin

Names

[ CAS No. ]:
67-20-9

[ Name ]:
Nitrofurantoin

[Synonym ]:
Hydantoin, 1-(5-nitro-furfurylideneamino)-
Furadantine
Nitrofurantoine
EINECS 200-646-5
NITROFURANTOIN
Furadonine
Macrodantin
Nitrofurantoina
1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
1-{[(1E)-(5-Nitrofuran-2-yl)methyliden]amino}imidazolidin-2,4-dion
Furophen T-Caps
Furadoin
Furantoina
Nitrofurantoin (JAN/USP)
1-{[(1E)-(5-nitrofuran-2-yl)méthylidène]amino}imidazolidine-2,4-dione
1-{[(E)-(5-Nitro-2-furyl)methylene]amino}-2,4-imidazolidinedione
2,4-Imidazolidinedione, 1-[[(1E)-(5-nitro-2-furanyl)methylene]amino]-
Nitrofurantoin [USAN:BAN:INN:JAN]
1-{[(E)-(5-Nitro-2-furyl)methylene]amino}imidazolidine-2,4-dione
Nitrofuradantin
1-{(E)-[(5-Nitro-2-furyl)methylene]amino}-2,4-imidazolidinedione
5-Nitrofurantoin
Nitrofurantoina [DCIT]
Furadoine
1-{[(E)-(5-nitrofuran-2-yl)methylidene]amino}imidazolidine-2,4-dione
MFCD00003224

Biological Activity

[Description]:

Nitrofurantoin is an antibiotic usually used to treat urinary tract infections.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Bacterial

Research Areas >> Infection

[References]

[1]. Garau J. Other antimicrobials of interest in the era of extended-spectrum beta-lactamases: fosfomycin, nitrofurantoin and tigecycline. Clin Microbiol Infect. 2008 Jan;14 Suppl 1:198-202.

[2]. Gupta K, et al. Increasing prevalence of antimicrobial resistance among uropathogens causing acute uncomplicated cystitis in women. JAMA. 1999 Feb 24;281(8):736-8.

[3]. Gupta K, et al. International clinical practice guidelines for the treatment of acute uncomplicated cystitis and pyelonephritis in women: A 2010 update by the Infectious Diseases Society of America and the European Society for Microbiology and Infectious

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Melting Point ]:
268°C

[ Molecular Formula ]:
C₈H₆N₄O₅

[ Molecular Weight ]:
238.157

[ Exact Mass ]:
238.033813

[ PSA ]:
120.73000

[ LogP ]:
-0.40

[ Index of Refraction ]:
1.745

[ Storage condition ]:
0-6°C

[ Stability ]:
Stability Stable, but light-sensitive. Combustible. Incompatible with strong oxidizing agents, strong alkalies, strong acids. Decomposes upon contact with most metals other than stainless steel and aluminium.

[ Water Solubility ]:
<0.01 g/100 mL at 19 ºC

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MU2800000

CHEMICAL NAME :: Hydantoin, 1-((5-nitrofurfurylidene)amino)-

CAS REGISTRY NUMBER :: 67-20-9

LAST UPDATED :: 199706

DATA ITEMS CITED :: 79

MOLECULAR FORMULA :: C8-H6-N4-O5

MOLECULAR WEIGHT :: 238.18

WISWESSER LINE NOTATION :: T5OJ BNW E1UN- AT5NVMV EHJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 40 mg/kg/2W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - interstitial nephritis Kidney, Ureter, Bladder - proteinuria Blood - changes in leukocyte (WBC) count

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 80 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - recording from peripheral motor nerve Behavioral - ataxia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 29 mg/kg/20D-I

TOXIC EFFECTS :: Brain and Coverings - increased intracranial pressure Sense Organs and Special Senses (Eye) - visual field changes Behavioral - somnolence (general depressed activity)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 24 mg/kg

TOXIC EFFECTS :: Blood - other hemolysis with or without anemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 42 mg/kg/6W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse Liver - jaundice, other or unclassified Liver - liver function tests impaired

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human

DOSE/DURATION :: 60 mg/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes in urine composition

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 604 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 112 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 360 mg/kg

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

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 53 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 250 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3500 mg/kg/14D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 45500 mg/kg/13W-I

TOXIC EFFECTS :: Liver - changes in liver weight Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 63 gm/kg/14D-I

TOXIC EFFECTS :: Behavioral - food intake (animal) Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3276 mg/kg/13W-I

TOXIC EFFECTS :: Liver - changes in liver weight Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10815 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 21630 mg/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 135 gm/kg/2Y-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 140 mg/kg

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

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2100 mg/kg

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

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - other effects on male

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1740 mg/kg

SEX/DURATION :: male 8 week(s) pre-mating female 2 week(s) pre-mating - 2 week(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1920 mg/kg

SEX/DURATION :: male 8 week(s) pre-mating female 2 week(s) pre-mating - 3 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 105 gm/kg

SEX/DURATION :: female 43 week(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 87500 ug/kg

SEX/DURATION :: male 5 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 75 mg/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - skin and skin appendages

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 750 mg/kg

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

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: DNA damage

TYPE OF TEST :: DNA damage

TYPE OF TEST :: Sperm Morphology

TYPE OF TEST :: DNA damage

TYPE OF TEST :: Sister chromatid exchange

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 200 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 225,181,1989 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,211,1990 IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,211,1990 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 50,211,1990 TOXICOLOGY REVIEW CCSUDL Carcinogenesis--A Comprehensive Survey. (Raven Press, 1185 Ave. of the Americas, New York, NY 10036) V.1- 1976- Volume(issue)/page/year: 4,171,1978 TOXICOLOGY REVIEW CRTXB2 CRC Critical Reviews in Toxicology. (CRC Press, Inc., 2000 Corporate Blvd., NW, Boca Raton, FL 33431) V.1- 1971- Volume(issue)/page/year: 2,365,1973 TOXICOLOGY REVIEW TRBMAV Texas Reports on Biology and Medicine. (Galveston, TX) V.1-41(2), 1943-81/82. Discontinued. Volume(issue)/page/year: 25,270,1967 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84411 No. of Facilities: 171 (estimated) No. of Industries: 1 No. of Occupations: 5 No. of Employees: 3756 (estimated) No. of Female Employees: 2239 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H317-H334

[ Precautionary Statements ]:
P261-P280-P342 + P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22;R42/43

[ Safety Phrases ]:
S22-S36/37-S45

[ RIDADR ]:
2811

[ WGK Germany ]:
3

[ RTECS ]:
MU2800000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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