An H2S-releasing latanoprost analog
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ACS 67

Item No. 13619

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-4-(3-thioxo-3H-1,2-dithiol-5-yl)phenyl ester, 5Z-heptenoic acid
CAS Number
1088434-86-9
Molecular Formula
C32H38O5S3
Formula Weight
598.8
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 2 mg/ml
λmax
210, 321, 434 nm
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(OC2=CC=C(C3=CC(SS3)=S)C=C2)=O)[C@@H](CC[C@@H](O)CCC4=CC=CC=C4)[C@H](O)C1
InChi Code
InChI=1S/C32H38O5S3/c33-24(15-12-22-8-4-3-5-9-22)16-19-27-26(28(34)20-29(27)35)10-6-1-2-7-11-31(36)37-25-17-13-23(14-18-25)30-21-32(38)40-39-30/h1,3-6,8-9,13-14,17-18,21,24,26-29,33-35H,2,7,10-12,15-16,19-20H2/b6-1-/t24-,26+,27+,28-,29+/m0/s1
InChi Key
JEEWZRQQYWVJCX-WEWVERJPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    Latanoprost is an F-series prostaglandin (PG) analog which has been approved for use as an ocular hypotensive drug for the treatment of glaucoma.1 Latanoprost is an isopropyl ester, a prodrug form which is converted to latanoprost (free acid) by endogenous esterase enzymes. The free acid form is 200 times more potent than latanoprost as an FP receptor ligand for the human recombinant FP receptor.2 ACS 67 is an analog of latanoprost (free acid) that contains a hydrogen sulfide releasing component conjugated to the latanoprost carboxyl group.3 In glaucomatous pigmented rabbits, ACS 67 reduced intra-ocular pressure (IOP) more rapidly and to a greater extent than latanoprost (15 versus 25.5 mm Hg at four hours) at a dose of 0.005% for each compound.3 ACS 67 also increased the levels of reduced glutathione and cGMP in the aqueous humor of glaucomatous pigmented rabbits better than latanoprost.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17(8), 691-704 (1992).

    2. Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim. Biophys. Acta 1483(2), 285-293 (2000).

    3. Perrino, E., Uliva, C., Lanzi, C., et al. New prostaglandin derivative for glaucoma treatment. Bioorg. Med. Chem. Lett. 19(6), 1639-1642 (2009).