Aristolochic acid A

Modify Date: 2024-01-02 11:38:05

Aristolochic acid A Structure
Aristolochic acid A structure
Common Name Aristolochic acid A
CAS Number 313-67-7 Molecular Weight 341.27
Density 1.6±0.1 g/cm3 Boiling Point 615.5±55.0 °C at 760 mmHg
Molecular Formula C17H11NO7 Melting Point 260 °C
MSDS Chinese USA Flash Point 326.0±31.5 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Aristolochic acid A


Aristolochic acid A (Aristolochic acid I) is the main component of plant extract Aristolochic acids, which are found in various herbal plants of genus Aristolochia and Asarum. AAI significantly reduces both activator protein 1 (AP-1) and NF-κB activities. Aristolochic acid A reduces BLCAP gene expression in human cell lines[1].

 Names

Name aristolochic acid
Synonym More Synonyms

 Aristolochic acid A Biological Activity

Description Aristolochic acid A (Aristolochic acid I) is the main component of plant extract Aristolochic acids, which are found in various herbal plants of genus Aristolochia and Asarum. AAI significantly reduces both activator protein 1 (AP-1) and NF-κB activities. Aristolochic acid A reduces BLCAP gene expression in human cell lines[1].
Related Catalog
In Vitro Aristolochic acid A (150, 200 μM, 24 hours) inhibits the cell viabilities of kidney cells HEK293 and HK-2[1]. Aristolochic acid A (100, 200 μM, 24 hours) causes a concentration-dependent decrease in bladder cancer-associated protein (BLCAP) mRNA levels in kidney cells (HEK 293 and HK-2) , and bladder cancer cell line (HT-1376)[1]. Aristolochic acid A (100, 200 μM, 24 hours) weakens the BLCAP protein signals in a dose-dependent manner in both HEK293 and HT-1376 cells[1]. Cell Viability Assay[1] Cell Line: Kidney cells (HEK 293 and HK-2) Concentration: 50, 100, 150, 200 μM Incubation Time: 24 hours Result: The cell viabilities of HEK293 and HK-2 were lower than that of vehicle-treated cultures until 150 μM and 200 μM. RT-PCR[1] Cell Line: Kidney cells (HEK 293 and HK-2), and bladder cancer cell line (HT-1376) Concentration: 100, 200 μM Incubation Time: 24 hours Result: Down regulated the levels of BLCAP mRNA. Western Blot Analysis[1] Cell Line: HEK293 and HT-1376 cells Concentration: 100, 200 μM Incubation Time: 24 hours Result: Reduced the BLCAP protein expression in a dose-dependent manner.
References

[1]. Huang YT, et al. Aristolochic acid I interferes with the expression of BLCAP tumor suppressor gene in human cells. Toxicol Lett. 2018 Jul;291:129-137.

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 615.5±55.0 °C at 760 mmHg
Melting Point 260 °C
Molecular Formula C17H11NO7
Molecular Weight 341.27
Flash Point 326.0±31.5 °C
Exact Mass 341.053558
PSA 110.81000
LogP 3.41
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.747
Water Solubility DMSO: soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CF3325000
CHEMICAL NAME :
Aristolochine
CAS REGISTRY NUMBER :
313-67-7
BEILSTEIN REFERENCE NO. :
0345159
LAST UPDATED :
199612
DATA ITEMS CITED :
20
MOLECULAR FORMULA :
C17-H11-N-O7
MOLECULAR WEIGHT :
341.29
WISWESSER LINE NOTATION :
T C5 B666 DO FO EHJ IVQ KNW NO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3 mg/kg/2D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
184 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
74 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
55900 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14320 ug/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 :
38400 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
40 mg/kg
TOXIC EFFECTS :
Vascular - BP elevation not characterized in autonomic section Lungs, Thorax, or Respiration - respiratory depression Lungs, Thorax, or Respiration - respiratory stimulation
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1500 ug/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - muscle weakness Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
22 mg/kg/11D-I
TOXIC EFFECTS :
Blood - changes in other cell count (unspecified) Skin and Appendages - dermatitis, other (after systemic exposure)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
105 mg/kg/3W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Gastrointestinal - tumors
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
DNA adduct
TYPE OF TEST :
Mutation in mammalian somatic cells
TYPE OF TEST :
Mutation in mammalian somatic cells

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
50 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 206,447,1988

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T:Toxic
Risk Phrases R25
Safety Phrases S7-S35-S45
RIDADR UN 1544 6.1/PG 3
WGK Germany 3
RTECS CF3325000
Packaging Group III
Hazard Class 6.1(b)

 Articles39

More Articles
Bardoxolone methyl (BARD) ameliorates aristolochic acid (AA)-induced acute kidney injury through Nrf2 pathway.

Toxicology 318 , 22-31, (2014)

Bardoxolone methyl (BARD) is an antioxidant modulator that acts through induction of the nuclear factor erythroid 2-related factor 2 (Nrf2) signaling pathway. This study aimed to investigate the role ...

Baicalin Protects Mice from Aristolochic Acid I-Induced Kidney Injury by Induction of CYP1A through the Aromatic Hydrocarbon Receptor.

Int. J. Mol. Sci. 16 , 16454-68, (2015)

Exposure to aristolochic acid I (AAI) can lead to aristolochic acid nephropathy (AAN), Balkan endemic nephropathy (BEN) and urothelial cancer. The induction of hepatic CYP1A, especially CYP1A2, was co...

Association of blood lead and mercury with estimated GFR in herbalists after the ban of herbs containing aristolochic acids in Taiwan.

Occup. Environ. Med. 70(8) , 545-51, (2013)

This study was undertaken to explore the association of estimated glomerular filtration rate (GFR) with exposure to aristolochic acids (ALAs) and nephrotoxic metals in herbalists after the ban of herb...

 Synonyms

Aristolohic Acid A
Descresept
8-methoxy-3,4-methylenedioxy-10-nitrophenanthrene-1-carboxylic acid
Aristolochic acid
birthwort
Phenanthro[3,4-d]-1,3-dioxole-5-carboxylic acid, 8-methoxy-6-nitro-
AristolochicacidI
EINECS 206-238-3
Aristolochia
tardolyt
Aristolochic Acid A
Aristolochia A
aristolochin
8-Methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylic acid
TR 1736
Aristolochic
MFCD00004996
aristolochine
8-Methoxy-6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid
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