Demeclocycline (hydrochloride) (CAS 64-73-3) | Cayman Chemical
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Demeclocycline (hydrochloride)

Item № 21759
CAS № 64-73-3
Purity ≥90%
product image
                (CAS 64-73-3)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     500 mg $69.00 0.00
     1 g $90.00 0.00

Pricing updated 2019-02-20. Prices are subject to change without notice.

Description
Synonyms
  • Demethylchlortetracycline
  • Demethyltetracycline

Demeclocycline is a broad-spectrum tetracycline antibiotic produced by S. aureofaciens.1 It has antimicrobial activity against ~3,200 pathogenic Gram-positive and Gram-negative bacteria in vitro that is 2-fold greater than that of tetracycline (Item No. 14328). The bactericidal action of demeclocycline is comparable to that of chlortetracycline but the duration of action is longer due to its resistance to degradation by acids or alkalis. It is effective against S. pyogenes and K. pneumoniae infections in vivo when administered orally or subcutaneously in mice. Demeclocycline decreases aquaporin 2 (AQP2) water channel gene transcription and protein abundance in mpkCCD murine collecting duct cells in a dose-dependent manner.2 It also increases urine volume, decreases urine osmolity, and increases fractional excretion of water in a rat model of hyponatremia. Formulations containing demeclocycline have been used to treat hyponatremia due to syndrome of inappropriate antidiuretic hormone secretion (SIADH) and as endodontic antibiotics to prevent infection following root canal procedures.3,4

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Technical Information
Formal Name
(4S,4aS,5aS,6S,12aS)-7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-1,11-dioxo-2-naphthacenecarboxamide, monohydrochloride
CAS Number
64-73-3
Synonyms
  • Demethylchlortetracycline
  • Demethyltetracycline
Molecular Formula
C21H21ClN2O8 • HCl
Formula Weight
501.3
Purity
≥90%
Formulation
A crystalline solid
λmax
229, 266, 369 nm
SMILES
O[C@H](C1=C(C2=O)C(O)=CC=C1Cl)[C@]3([H])C2=C(O)[C@@](C(C(C(N)=O)=C(O)[C@H]4N(C)C)=O)(O)[C@@]4([H])C3.Cl
InChI Code
InChI=1S/C21H21ClN2O8.ClH/c1-24(2)14-7-5-6-10(16(27)12-9(25)4-3-8(22)11(12)15(6)26)18(29)21(7,32)19(30)13(17(14)28)20(23)31;/h3-4,6-7,14-15,25-26,28-29,32H,5H2,1-2H3,(H2,23,31);1H/t6-,7-,14-,15-,21-;/m0./s1
InChI Key
GVSJQNRGSCOSNJ-KBHRXELFSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

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References & Product Citations
Product Description References

1. Finland, M., and Garrod, L.P. Demethylchlortetracycline Br. Med. J. 2(5204), 959-963 (1960).

2. Kortenoeven, M.L.A., Sinke, A.P., Hadrup, N., et al. Demeclocycline attenuates hyponatremia by reducing aquaporin-2 expression in the renal inner medulla Am. J. Physiol. Renal Physiol. 305(12), F1705-F1718 (2013).

3. Athanassiadis, B., Abbott, P.V., George, N., et al. An in vitro study of the antimicrobial activity of some endodontic medicaments and their bases using an agar well diffusion assay Aust. Dent. J. 54(2), 141-146 (2009).

4. Grant, P., Ayuk, J., Bouloux, P.-M., et al. The diagnosis and management of inpatient hyponatraemia and SIADH Eur. J. Clin. Invest. 45(8), 888-894 (2015).

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