CAS 13292-46-1|Rifampicin

Introduction：Basic information about CAS 13292-46-1|Rifampicin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Rifampicin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles624
8. Synonyms

Common Name	Rifampicin
CAS Number	13292-46-1	Molecular Weight	822.940
Density	1.3±0.1 g/cm3	Boiling Point	1004.4±65.0 °C at 760 mmHg
Molecular Formula	C₄₃H₅₈N₄O₁₂	Melting Point	183ºC (dec.)
MSDS	ChineseUSA	Flash Point	561.3±34.3 °C
Symbol	GHS07	Signal Word	Warning

Names

Name	rifampicin
Synonym	More Synonyms

Rifampicin BiologicalActivity

Description	Rifampicin is a potent and broad spectrum antibiotic against bacterial pathogens.
Related Catalog	Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection
In Vitro	Rifampicin (100 mg/mL) can block the functional activity of P-glycoprotein. Rifampicin is not a substract for P-glycoprotein. The mechanism of rifampicin resistance is unassociated with the functional activity of P-glycoprotein[3].
In Vivo	Rifampicin (200, 400 mg/kg) can induce fatty liver at high concentration[1]. Rifampicin (30 mg/kg, i.p.) treatment of S464P biofilms in vivo results in a slight decline, but earlier rebinds in bioluminescence from these catheters compared with the parental signal, whereas rifampicin has no affect on bioluminescence in mice infected with mutant H481Y[2].
Animal Admin	Briefly, 1 cm Teflon catheter (14-gauge) carrying 104 cfu S. aureus, either the parental strain Xen 29 or the RifR mutants S464P or H481Y, are implanted subcutaneously in groups of nine mice per strain. One catheter segment is inserted on each side of each animal. Six days after the implantation of the catheters, five mice from each group are treated with rifampicin at 30 mg/kg intraperitoneally in 0.1 mL saline, twice daily for four consecutive days. The remaining four mice in each group are left untreated as controls. At various time points during the infection, the mice are anaesthetized using a constant flow of 1.5% isoflurane from the IVIS® manifold, and imaged using an IVIS® Image System 100 Series. The bioluminescent signals (photons/s) emitted from the mice are analysed using LivingImage® software and plotted over the course of infection. The mice are sacrificed 20 days after infection (11 days after final rifampicin treatment). The catheters are surgically removed and the bacteria are detached by sonication for determination of bacterial burdens on the catheters.
References	[1]. Piriou A, et al. Fatty liver induced by high doses of rifampicin in the rat: possible relation with an inhibition of RNA polymerases in eukariotic cells. Arch Toxicol Suppl. 1979;(2):333-7. [2]. Yu J, et al. Monitoring in vivo fitness of rifampicin-resistant Staphylococcus aureus mutants in a mouse biofilm infection model. J Antimicrob Chemother. 2005 Apr;55(4):528-34. Epub 2005 Mar 2. [3]. Erokhina MV, et al. [In vitro development of rifampicin resistance in the epithelial cells]. Probl Tuberk Bolezn Legk. 2006;(8):58-61.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	1004.4±65.0 °C at 760 mmHg
Melting Point	183ºC (dec.)
Molecular Formula	C₄₃H₅₈N₄O₁₂
Molecular Weight	822.940
Flash Point	561.3±34.3 °C
Exact Mass	822.405151
PSA	220.15000
LogP	1.09
Vapour Pressure	0.0±0.3 mmHg at 25°C
Index of Refraction	1.613
InChIKey	JQXXHWHPUNPDRT-WACSZCHISA-N
SMILES	COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(c(C=NN5CCN(C)CC5)c(O)c4c3C2=O)NC(=O)C(C)=CC=CC(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C1C
Storage condition	2-8°C
Water Solubility	chloroform: soluble50mg/mL, clear

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VJ7000000

CHEMICAL NAME :: Rifomycin SV, 8-(N-(4-methyl-1-piperazinyl)formidoyl)-

CAS REGISTRY NUMBER :: 13292-46-1

LAST UPDATED :: 199607

DATA ITEMS CITED :: 60

MOLECULAR FORMULA :: C43-H58-N4-O12

MOLECULAR WEIGHT :: 823.05

WISWESSER LINE NOTATION :: T C6 B65-24- A D E 2BC G& AV LO NO F&VM OU B&U D&U MH&&&TJ DQ GQ IQ JI MI QO1 R1 SOV1 T1 UQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 504 mg/kg/42D-I

TOXIC EFFECTS :: Behavioral - muscle weakness Lungs, Thorax, or Respiration - dyspnea Blood - aplastic anemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 315 mg/kg/5W-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - conjunctive irritation Sense Organs and Special Senses (Eye) - iritis Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 13 mg/kg/2D

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 857 mg/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting Gastrointestinal - other changes Skin and Appendages - dermatitis, other (after systemic exposure)

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1570 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 :: 511 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 534 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 :: 500 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 :: 416 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 621 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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 260 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 - rabbit

DOSE/DURATION :: 2120 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 - guinea pig

DOSE/DURATION :: 639 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 :: 4 gm/kg/8D-I

TOXIC EFFECTS :: Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 17500 mg/kg/5W-I

TOXIC EFFECTS :: Liver - fatty liver degeneration Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 72800 mg/kg/26W-I

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Related to Chronic Data - death

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 mg/m3/4H/17W-I

TOXIC EFFECTS :: Cardiac - changes in heart weight Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - changes in lung weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 280 mg/kg/14D-I

TOXIC EFFECTS :: Liver - change in gall bladder structure or function Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 7800 mg/kg/26W-I

TOXIC EFFECTS :: Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 19005 mg/kg/26W-I

TOXIC EFFECTS :: 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 - rabbit

DOSE/DURATION :: 11200 mg/kg/4W-I

TOXIC EFFECTS :: Liver - jaundice, other or unclassified Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5600 mg/kg/8D-I

TOXIC EFFECTS :: Liver - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 5 mg/m3/4H/17W-I

TOXIC EFFECTS :: Cardiac - changes in heart weight Lungs, Thorax, or Respiration - fibrosis, focal (pneumoconiosis) Lungs, Thorax, or Respiration - changes in lung weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8400 mg/kg/60W-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1400 mg/kg

SEX/DURATION :: female 4-10 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3200 mg/kg

SEX/DURATION :: female 1-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 gm/kg

SEX/DURATION :: female 2-21 day(s) after conception

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 800 mg/kg

SEX/DURATION :: female 9-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - Central Nervous System Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

DOSE :: 6100 ug/m3/24H

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2200 mg/kg

SEX/DURATION :: female 6-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2600 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

MUTATION DATA

TYPE OF TEST :: Host-mediated assay

TEST SYSTEM :: Rodent - mouse Ascites tumor

DOSE/DURATION :: 5 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 141,171,1984 *** 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: 24,243,1980 IARC Cancer Review:Human No Adequate Data 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: 24,243,1980 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 TOXICOLOGY REVIEW MMWOAU Muenchener Medicinische Wochenschrift. (Munich, Fed. Rep. Ger.) V.33-115, 1886-1973. Volume(issue)/page/year: 115,1685,1973 TOXICOLOGY REVIEW LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 2,1285,1980 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4882 No. of Facilities: 141 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 928 (estimated) No. of Female Employees: 656 (estimated)

Safety Information

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H302
Precautionary Statements	P301 + P312 + P330
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R22;R36/37/38
Safety Phrases	S26-S36
RIDADR	NONH for all modes of transport
WGK Germany	3
RTECS	VJ7000000
HS Code	2941903000

Customs

HS Code	2941903000

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Synonyms

(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-Pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methyl-1-piperazinyl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyc ;lo[23.3.1.1.0]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate

rifobac

Rimactane

arficin

2,7-(Epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,11(2H)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[(E)-[(4-methyl-1-piperazinyl)imino]methyl]-, (2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-

Rifampicin

FaMcin

rifinah

Eremfat

Rimactan

rifagen

MFCD00151389

Rifamycin AMP

3-[[(4-Methyl-1-piperazinyl)imino]methyl]rifamycin

Rifadine

RIF

3-(4-Methylpiperazinyliminomethyl)rifamycin SV,Rifampin,Rifamycin AMP

(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-Pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methyl-1-piperazinyl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate

(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E)-2,15,17,27,29-Pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate

Rifa

(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),1(29),2,4,9,19,21,25,27-nonaen-13-yl acetate

UNII-VJT6J7R4TR

(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-Pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.1.0]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate

2,7-(epoxy[1,11,13]pentadecatrienoimino)naphtho[2,1-b]furan-1,11(2H)-dione, 21-(acetyloxy)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-[(E)-[(4-methyl-1-piperazinyl)imino]methyl]-, (2S,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-

EINECS 236-312-0

(2S,12Z,14E,16S,17S,18R,19R,20R,21S,22R,23S,24E)-5,6,9,17,19-pentahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-1,11-dioxo-1,2-dihydro-2,7-(epoxypentadeca[1,11,13]trienoimino)naphtho[2,1-b]furan-21-yl acetate

Abrifam

Rifampin

RIFADIN

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