Ketoconazole - ≥98%, high purity , CAS No.65277-42-1, Inhibitor of CYP3A4;Channel blocker of K v1.8

Item Number
K129737
Grouped product items
SKUSizeAvailabilityPrice Qty
K129737-1g
1g
In stock
$128.90
K129737-5g
5g
In stock
$441.90
K129737-10g
10g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$795.90
K129737-25g
25g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$1,790.90
K129737-100g
100g
In stock
$6,444.90
K129737-500g
500g
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
$28,999.90

Potent cytochrome P450 inhibitor. Antifungal agent.

Basic Description

SynonymsHMS3678J17 | Ketoconazole (k) | KTZ | MLS002222255 | N-(1,3,4-Trihydroxyoctadecan-2-yl)octadecanimidic acid | NCGC00025000-08 | SW196888-4 | ketoconazole | Opera_ID_397 | Prestwick0_000389 | NCGC00253967-01 | 1-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)
Specifications & PurityMoligand™, ≥98%
Biochemical and Physiological MechanismsPotent cytochrome P450 inhibitor (K i values are 26.7 and 109 nM at CYP3A4 and CYP3A5, respectively). Antifungal agent. Additionally, shows activity at human androgen receptors.
Storage TempStore at 2-8°C
Shipped InWet ice
GradeMoligand™
Action TypeCHANNEL BLOCKER, INHIBITOR
Mechanism of actionInhibitor of CYP3A4;Channel blocker of K v1.8
NoteWherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description

Ketoconazole is an imidazole-containing small molecule inhibitor of cytochrome P-450-dependent steps in the biosynthesis of steroid hormones; also inhibits TXA Synthase (thromboxane synthetase) and 5-LO (5-lipoxygenase) activity. Ketoconazole exhibits antimetastatic, antineoplastic, and antipsoriatic activity. Inhibition of 5-LO (5-lipoxygenase) by Ketoconazole interrupts arachidonic acid -derived leukotriene production, which was correlated to a suppression of leukotriene-mediated anaphylactic bronchoconstriction in guinea pigs. Ketoconazole is described as reducing platelet cellular levels of thromboxane A2, suppressing thromboxane A2-mediated increase of microvascular permeability in response to ischemia insults. Ketoconazole produces an antiandrogen effect through inhibition of adrenocorticoid biosynthesis, suppressing the adrenal secretion of androgens and attenuating cortisol response. Ketoconazole is an inhibitor of CYP17A1, CYP3A4 and CYP3A5
An inhibitor of CYP proteins, thromboxane synthetase, and 5-LO

Associated Targets(Human)

CYP2D6 Tclin Cytochrome P450 2D6 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP24A1 Tchem 1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP3A4 Tclin Cytochrome P450 3A4 (36 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP3A5 Tclin Cytochrome P450 3A5 (4 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP19A1 Tclin Aromatase (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
CYP17A1 Tclin Steroid 17-alpha-hydroxylase/17,20 lyase (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
KCNA10 Tclin Potassium voltage-gated channel subfamily A member 10 (1 Activities)
Activity TypeActivity Value -log(M)Mechanism of ActionActivity ReferencePublications (PubMed IDs)
HMGCR Tclin HMG-CoA reductase (2475 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP19A1 Tclin Cytochrome P450 19A1 (6099 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C8 Tchem Cytochrome P450 2C8 (1492 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HMOX2 Tchem Heme oxygenase 2 (250 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HMOX1 Tchem Heme oxygenase 1 (32 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A5 Tclin Cytochrome P450 3A5 (525 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP17A1 Tclin Cytochrome P450 17A1 (3627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2E1 Tchem Cytochrome P450 2E1 (2174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MES-SA/Dx5 (643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U2OS (164939 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP (8286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ASPC1 (1310 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCG2 Tchem ATP-binding cassette sub-family G member 2 (4927 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ABCB11 Tchem Bile salt export pump (2311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4/3A5 (100 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Keap1/Nrf2 (1722 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK-293T (167025 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP8B1 Tchem 7-alpha-hydroxycholest-4-en-3-one 12-alpha-hydroxylase (91 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp24a1 Cytochrome P450 24A1 (20 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Fusarium solani (1274 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus flavus (8875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus niger (16508 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus cereus (7522 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pichia kudriavzevii (7448 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Kluyveromyces marxianus (909 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Penicillium chrysogenum (1593 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus fumigatus (16427 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cryptococcus neoformans (21258 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Nakaseomyces glabratus (9108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida parapsilosis (8521 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida tropicalis (8381 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Fusarium oxysporum (3998 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichoderma viride (1263 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania amazonensis (3813 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania braziliensis (1091 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania donovani (89745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania major (2877 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania mexicana (936 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Leishmania tropica (461 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Geotrichum candidum (421 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Talaromyces funiculosus (619 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus ochraceus (560 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lichtheimia corymbifera (940 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Botrytis cinerea (4183 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NIH3T3 (5395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyp3a2 Cytochrome P450 3A2 (13 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Alternaria alternata (757 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
[Candida] sake (415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Curvularia lunata (722 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Colletotrichum gloeosporioides (560 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Penicillium ochrochloron (549 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Penicillium verrucosum (38 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sclerotinia sclerotiorum (877 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trichophyton mentagrophytes (4846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Valsa mali (129 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Corynespora cassiicola (104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus versicolor (452 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP51 Sterol 14-alpha demethylase (857 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
INCHI InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1
InChi Key XMAYWYJOQHXEEK-OZXSUGGESA-N
Canonical SMILES CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
Isomeric SMILES CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
WGK Germany 3
RTECS TK7912300
PubChem CID 456201
Molecular Weight 531.43
Reaxy-Rn 5488107

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Find and download the COA for your product by matching the lot number on the packaging.

17 results found

Lot NumberCertificate TypeDateItem
G2423154Certificate of AnalysisJul 26, 2024 K129737
G2227239Certificate of AnalysisMay 20, 2024 K129737
G2227241Certificate of AnalysisMay 20, 2024 K129737
G2227242Certificate of AnalysisMay 20, 2024 K129737
G2227270Certificate of AnalysisMay 20, 2024 K129737
G2227240Certificate of AnalysisMay 13, 2024 K129737
G2425490Certificate of AnalysisMar 25, 2024 K129737
G2425489Certificate of AnalysisMar 25, 2024 K129737
G2425488Certificate of AnalysisMar 25, 2024 K129737
D2422220Certificate of AnalysisMar 25, 2024 K129737
F2125353Certificate of AnalysisApr 13, 2023 K129737
F2125352Certificate of AnalysisApr 13, 2023 K129737
F2125354Certificate of AnalysisApr 13, 2023 K129737
H2005074Certificate of AnalysisJun 17, 2022 K129737
G2311055Certificate of AnalysisJun 15, 2022 K129737
H2311033Certificate of AnalysisJun 15, 2022 K129737
I2311025Certificate of AnalysisJun 15, 2022 K129737

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Chemical and Physical Properties

SolubilitySoluble in DMSO (20 mg/mL warm), ethanol (20 mg/mL warm), chloroform, water (<1 mg/mL), and methanol
Sensitivityheat sensitive
Melt Point(°C)150 °C

Safety and Hazards(GHS)

Pictogram(s) GHS06,   GHS08,   GHS09
Signal Danger
Hazard Statements

H301:Toxic if swallowed

H373:Causes damage to organs through prolonged or repeated exposure

H400:Very toxic to aquatic life

H410:Very toxic to aquatic life with long lasting effects

H360F:May damage fertility

Precautionary Statements

P273:Avoid release to the environment.

P280:Wear protective gloves/protective clothing/eye protection/face protection.

P321:Specific treatment (see ... on this label).

P405:Store locked up.

P501:Dispose of contents/container to ...

P264:Wash hands [and …] thoroughly after handling.

P260:Do not breathe dust/fume/gas/mist/vapors/spray.

P270:Do not eat, drink or smoke when using this product.

P391:Collect spillage.

P330:Rinse mouth.

P203:Obtain, read and follow all safety instructions before use.

P301+P316:IF SWALLOWED: Get emergency medical help immediately.

P318:if exposed or concerned, get medical advice.

P319:Get medical help if you feel unwell.

WGK Germany 3
RTECS TK7912300
Reaxy-Rn 5488107
Merck Index 5302

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20. Li Zhuo-Qing, Jiang Li-Long, Zhao Dong-Sheng, Zhou Jing, Wang Ling-Li, Wu Zi-Tian, Zheng Xian, Shi Zi-Qi, Li Ping, Li Hui-Jun.  (2018)  The Modulatory Role of CYP3A4 in Dictamnine-Induced Hepatotoxicity.  Frontiers in Pharmacology,    [PMID:30283337] [10.3389/fphar.2018.01033]
21. Y.W. Liu, Y. Chen, X.H. Chen, Z.N. Yang, Y. Xie, Z. Zhang.  (2018)  Study on adsorption behavior of ketoconazole on Q235 mild steel in 1.0 M HCl solution with electrochemical measurement.  JOURNAL OF ALLOYS AND COMPOUNDS,  758  (184).  [PMID:] [10.1016/j.jallcom.2018.05.107]
22. Qingling Cui, Yingni Pan, Xiaowei Yan, Bao Qu, Xiaoqiu Liu, Wei Xiao.  (2017)  A metabolic way to investigate related hurdles causing poor bioavailability in oral delivery of isoacteoside in rats employing ultrahigh-performance liquid chromatography/quadrupole time-of-flight tandem mass spectrometry.  RAPID COMMUNICATIONS IN MASS SPECTROMETRY,  31  (4): (371-380).  [PMID:27859774] [10.1002/rcm.7795]
23. Lili Wu, Wanping Zhong, Junjin Liu, Weichao Han, Shilong Zhong, Qiang Wei, Shuwen Liu, Lan Tang.  (2015)  Human microsomal cyttrochrome P450-mediated reduction of oxysophocarpine, an active and highly toxic constituent derived from Sophora flavescens species, and its intestinal absorption and metabolism in rat.  FITOTERAPIA,  105  (26).  [PMID:26045316] [10.1016/j.fitote.2015.05.021]
24. Hang Xue,Liangcong Hu,Yuan Xiong,Xiangwei Zhu,Congying Wei,Faqi Cao,Wu Zhou,Yun Sun,Yori Endo,Mengfei Liu,Yi Liu,Jing Liu,Abudula Abududilibaier,Lang Chen,Chenchen Yan,Bobin Mi,Guohui Liu.  (2019-10-05)  Quaternized chitosan-Matrigel-polyacrylamide hydrogels as wound dressing for wound repair and regeneration..  Carbohydrate polymers,  226  (115302-115302).  [PMID:31582049]

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25. Hang Xue,Liangcong Hu,Yuan Xiong,Xiangwei Zhu,Congying Wei,Faqi Cao,Wu Zhou,Yun Sun,Yori Endo,Mengfei Liu,Yi Liu,Jing Liu,Abudula Abududilibaier,Lang Chen,Chenchen Yan,Bobin Mi,Guohui Liu.  (2019-10-05)  Quaternized chitosan-Matrigel-polyacrylamide hydrogels as wound dressing for wound repair and regeneration..  Carbohydrate polymers,  226  (115302-115302).  [PMID:31582049]

Solution Calculators