Deoxypyridinoline

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Deoxypyridinoline
Deoxypyridinoline.svg
Names
Systematic IUPAC name
(2R)-6-{3-[(3S)-3-Amino-3-carboxypropyl]-4-[(2S)-2-amino-3-carboxyethyl]-5-hydroxypyridin-1-ium-1-yl}hexanoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H28N4O7/c19-12(16(24)25)3-1-2-6-22-8-10(4-5-13(20)17(26)27)11(15(23)9-22)7-14(21)18(28)29/h8-9,12-14H,1-7,19-21H2,(H3-,23,24,25,26,27,28,29)/t12-,13+,14+/m1/s1
    Key: ZAHDXEIQWWLQQL-RDBSUJKOSA-N
  • C1=C(C(=C(C=[N+]1CCCC[C@H](C(=O)[O-])N)O)C[C@@H](C(=O)O)N)CC[C@@H](C(=O)O)N
Properties
C18H28N4O7
Molar mass 412.43752 g mol−1
Related compounds
Related compounds
 pyridinoline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


Deoxypyridinoline, also called D-Pyrilinks, Pyrilinks-D, or deoxyPYD, is one of two pyridinium cross-links that provide structural stiffness to type I collagen found in bones. [1] It is excreted unmetabolized in urine and is a specific marker of bone resorption and osteoclastic activity. It is measured in urine tests and is used along with other bone markers such as alkaline phosphatase, osteocalcin, and N-terminal telopeptide to diagnose bone diseases such as postmenopausal osteoporosis, bone metastasis, and Paget's disease, furthermore, it has been useful in monitoring treatments that contain bone-active agents such as estrogens and bisphosphonates. [1]

Certain studies have attempted to generate a standardization of Deoxypyridinoline via an individual molar absorptivity value at acid and neutrality pH. The result was 5160 and 5290 L mol−1 cm−1 respectively. [2]

References

  1. 1 2 Rubinacci, A; Melzi, R; Zampino, M; Soldarini, A; Villa, I (1999). "Total and free deoxypyridinoline after acute osteoclast activity inhibition". Clinical Chemistry. 45 (9): 1510–6. doi: 10.1093/clinchem/45.9.1510 . PMID   10471654.
  2. ↑ Robins, SP; Duncan, A; Wilson, N; Evans, BJ (1996). "Standardization of pyridinium crosslinks, pyridinoline and deoxypyridinoline, for use as biochemical markers of collagen degradation". Clinical Chemistry. 42 (10): 1621–6. doi: 10.1093/clinchem/42.10.1621 . PMID   8855145.
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