Cyclosporin L Related Compound 3

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Cyclosporin L Related Compound 3
Category Cyclosporin Analogue Set
Catalog number BBF-05755
CAS 174292-85-4
Molecular Weight 187.24
Molecular Formula C9H17NO3
Purity ≥90% by HPLC

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Description

Cyclosporin L Related Compound 3 is an impurity of cyclosporin, which is a calcineurin phosphatase pathway inhibitor, used as an immunosuppressant drug to prevent rejection in organ transplantation.

Specification

Synonyms (E)-(2R,3S,4R)-2-Amino-3-hydroxy-4-methyl-oct-6-enoic acid; (2R,3S,4R,6E)-2-amino-3-hydroxy-4-methyl-6-octenoic acid; 2-Amino-4-[(2E)-2-buten-1-yl]-2,4,5-trideoxy-L-arabinonic acid; L-Arabinonic acid, 2-amino-4-[(2E)-2-buten-1-yl]-2,4,5-trideoxy-
IUPAC Name (E,2R,3S,4R)-2-amino-3-hydroxy-4-methyloct-6-enoic acid
Canonical SMILES CC=CCC(C)C(C(C(=O)O)N)O
InChI InChI=1S/C9H17NO3/c1-3-4-5-6(2)8(11)7(10)9(12)13/h3-4,6-8,11H,5,10H2,1-2H3,(H,12,13)/b4-3+/t6-,7-,8+/m1/s1
InChI Key RPALEGQGCGCFCX-UAENDNOJSA-N

Properties

Boiling Point 376.8±42.0°C at 760 mmHg
Density 1.1±0.1 g/cm3

Reference Reading

1. Endoscopic ultrasound-guided inoculation of transmissible venereal tumor in the colon: A large animal model for colon neoplasia.
Bhutani MS1, Uthamanthil R, Suzuki R, Shetty A, Klumpp SA, Nau W, Stafford RJ. Endosc Ultrasound. 2016 Mar-Apr;5(2):85-93. doi: 10.4103/2303-9027.180471.
BACKGROUND: To develop and evaluate the feasibility of emerging interventions, animal models with accurate anatomical environment are required.
2. Modern approaches to the ocular delivery of cyclosporine A.
Agarwal P1, Rupenthal ID2. Drug Discov Today. 2016 Apr 11. pii: S1359-6446(16)30106-4. doi: 10.1016/j.drudis.2016.04.002. [Epub ahead of print]
Cyclosporine A (CsA) has long been the mainstay treatment for dry eye syndrome (DES), one of the most common disorders of the eye. However, the poor water solubility of CsA renders it difficult to formulate it into topical ocular dosage forms. Restasis® is currently the only US Food and Drug Administration (FDA)-approved CsA formulation, while Ikervis® has recently been launched in Europe, with both commonly associated with severe ocular discomfort. Therefore, several CsA formulations have been investigated with the aim to improve bioavailability while reducing adverse effects associated with the marketed formulations. In this review, we summarize recent advances in ocular CsA delivery that provide safer and more effective alternatives for the management of DES and other ocular inflammatory conditions.
3. Keratoconjunctivitis sicca exacerbation in a dog treated with systemic atenolol.
Barsotti G1, Vezzosi T1. J Small Anim Pract. 2016 Apr 13. doi: 10.1111/jsap.12477. [Epub ahead of print]
A 6-year-old, intact, male English cocker spaniel was referred for treatment of chronic conjunctivitis and unilateral keratitis. The dog was diagnosed with bilateral immune-mediated keratoconjunctivitis sicca, treated with topical cyclosporine 0·2% ointment and sodium hyaluronate eye drops and improved considerably. After 2 months, pulmonic stenosis was diagnosed, and the dog commenced treatment with oral atenolol; the ophthalmological disease worsened dramatically within a few days. The ophthalmic signs rapidly improved after discontinuation of atenolol, and there was bilateral complete remission after 3 weeks. No oral β-blocker therapy was reintroduced, and thereafter, keratoconjunctivitis sicca was well-controlled with topical therapy.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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