A metabolite of bosentan
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Parent Compound(s)
11731Bosentan
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Hydroxy Bosentan

Item No. 22366

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-(2-hydroxy-1,1-dimethylethyl)-N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)[2,2'-bipyrimidin]-4-yl]-benzenesulfonamide
CAS Number
253688-60-7
Synonyms
  • Ro 48-5033
  • Ro 48-8634
Molecular Formula
C27H29N5O7S
Formula Weight
567.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
COC1=CC=CC=C1OC2=C(NS(C3=CC=C(C(C)(CO)C)C=C3)(=O)=O)N=C(C4=NC=CC=N4)N=C2OCCO
InChi Code
InChI=1S/C27H29N5O7S/c1-27(2,17-34)18-9-11-19(12-10-18)40(35,36)32-23-22(39-21-8-5-4-7-20(21)37-3)26(38-16-15-33)31-25(30-23)24-28-13-6-14-29-24/h4-14,33-34H,15-17H2,1-3H3,(H,30,31,32)
InChi Key
FAJQMBCLPZWTQJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $127

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    1 mg

    $239

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    5 mg

    $932

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    Product Description

    Hydroxy bosentan is an active phase I metabolite of bosentan (Item No. 11731) produced by the cytochrome P450 isoforms CYP3A4 and CYP2C9.1,2 Bosentan is an antagonist of the endothelin receptors type A (Ki = 6.5 nM) and type B (Ki = 340 nM).3,4 Up to 20% of the activity of bosentan may be due to the action of hydroxy bosentan because even though it has a lower affinity for endothelin receptors, its concentration is 3-fold higher in plasma.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lepri, S., Goracci, L., Valeri, A., et al. Metabolism study and biological evaluation of bosentan derivatives. Eur. J. Med. Chem. 121, 658-670 (2016).

    2. Fahrmayr, C., König, J., Auge, D., et al. Phase I and II metabolism and MRP2-mediated export of bosentan in a MDCKII-OATP1B1-CYP3A4-UGT1A1-MRP2 quadruple-transfected cell line. Br. J. Pharmacol. 169(1), 21-33 (2013).

    3. Jae, H.S., Winn, M., Dixon, D.B., et al. Pyrrolidine-3-carboxylic acids as endothelin antagonists. 2. Sulfonamide-based ETA/ETB mixed antagonists. J. Med. Chem. 40(20), 3217-3227 (1997).

    4. Wu, C., Decker, E.R., Blok, H., et al. Discovery, modeling, and human pharmacokinetics of N-(2-acetyl-4,6-dimethylphenyl)-3-(3,4-dimethylisoxazol-5-ylsulfamoyl)-thiophene-2-carboxamide (TBC3711), a second generation, ETA selective, and orally bioavailable endothelin antagonist. J. Med. Chem. 47(8), 1969-1986 (2004).

    5. Dingemanse, J., and van Giergsbergen, L.M. Clinical pharmacology of bosentan, a dual endothelin receptor antagonist. Clin. Pharmacokinet. 43(15), 1089-1115 (2004).