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A4638

Sigma-Aldrich

Azathioprine

≥98%

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Synonym(s):
6-(1-Methyl-4-nitroimidazol-5-yl)thiopurine
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)

Quality Level

100

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

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
Laurent Peyrin-Biroulet et al.
Gut, 63(1), 88-95 (2013-08-27)
The Crohn's Disease Activity Index (CDAI) has been criticised due to heavy weighting on subjective clinical symptoms. C-reactive protein (CRP) and endoscopic lesions are objective measures of inflammation. We investigated the relationships between clinical disease activity, CRP normalisation and mucosal
Joanna Kitley et al.
Journal of neurology, neurosurgery, and psychiatry, 84(8), 918-921 (2013-03-08)
Neuromyelitis optica (NMO) is a severe autoimmune inflammatory disorder associated with considerable relapse-related disability. Immunosuppression is the mainstay of treatment but many patients do not tolerate first-line immunosuppressive agents, or experience ongoing relapses. To evaluate the effectiveness and tolerability of
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