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A4638

Sigma-Aldrich

Azathioprine

≥98%

Synonym(s):

6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine

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About This Item

Empirical Formula (Hill Notation):
C9H7N7O2S
CAS Number:
446-86-6
Molecular Weight:
277.26
EC Number:
207-175-4
MDL number:
MFCD00069203
UNSPSC Code:
12352202
PubChem Substance ID:
57653853
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98%

form

powder

solubility

1 M NH4OH: 20 mg/mL, clear to slightly hazy

storage temp.

−20°C

SMILES string

Cn1cnc(c1Sc2ncnc3[nH]cnc23)[N+]([O-])=O

InChI

1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)

InChI key

LMEKQMALGUDUQG-UHFFFAOYSA-N

Gene Information

human ... PPAT(5471)

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Biochem/physiol Actions

Has shown promise in treatment of alopecia areata (autoimmune hair loss), with no difference in effectiveness between genders.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Susan Farshi et al.
International journal of dermatology, 49(10), 1188-1193 (2010-10-05)
Alopecia areata is an autoimmune disease resulting in partial or total nonscarring hair loss and the treatment of severe alopecia areata is difficult. The aim of this study was to evaluate the efficacy and safety of azathioprine as a systemic
Björn Pasternak et al.
American journal of epidemiology, 177(11), 1296-1305 (2013-03-22)
Increased risks of lymphoma and skin cancer associated with thiopurine use among patients with inflammatory bowel disease have been shown, but data on the overall cancer risk are limited. We conducted a historical cohort study of 45,986 patients with inflammatory
Systemic therapies for severe atopic dermatitis in children and adults.
Carsten Flohr et al.
The Journal of allergy and clinical immunology, 132(3), 774-774 (2013-09-03)
Eliza Prefontaine et al.
The Cochrane database of systematic reviews, (6)(6), CD000545-CD000545 (2010-06-18)
The results from controlled clinical trials investigating the efficacy of azathioprine and 6-mercaptopurine for the treatment of active Crohn's disease were conflicting and controversial. A meta-analysis was performed to assess the effectiveness of these drugs for the induction of remission
Anne Bourrier et al.
Current drug targets, 14(12), 1471-1479 (2013-04-12)
Azathioprine is an efficient maintenance treatment of IBD, able to maintain a complete clinical and anatomical remission in about one third of patients. However there are concerns regarding its long term tolerance, particularly myelosuppression and malignancy. Azathioprine is not required
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