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    Levulan

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 5451-09-2, Aminolevulinic acid hydrochloride, Levulan, 5-amino-4-oxopentanoic acid hydrochloride, Levulan kerastick, 5-aminolevulinic acid hcl
    Molecular Formula
    C5H10ClNO3
    Molecular Weight
    167.59  g/mol
    InChI Key
    ZLHFONARZHCSET-UHFFFAOYSA-N
    FDA UNII
    V35KBM8JGR
    A compound produced from succinyl-CoA and GLYCINE as an intermediate in heme synthesis. It is used as a PHOTOCHEMOTHERAPY for actinic KERATOSIS.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-amino-4-oxopentanoic acid;hydrochloride
    2.1.2 InChI
    InChI=1S/C5H9NO3.ClH/c6-3-4(7)1-2-5(8)9;/h1-3,6H2,(H,8,9);1H
    2.1.3 InChI Key
    ZLHFONARZHCSET-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C(CC(=O)O)C(=O)CN.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    V35KBM8JGR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5 Aminolaevulinate

    2. 5 Aminolevulinate

    3. 5-aminolaevulinate

    4. 5-aminolevulinate

    5. Acid Hydrochloride, Aminolevulinic

    6. Acid, Aminolevulinic

    7. Acid, Delta-aminolevulinic

    8. Aminolevulinic Acid

    9. Aminolevulinic Acid Hydrochloride

    10. Delta Aminolevulinic Acid

    11. Delta-aminolevulinic Acid

    12. Hydrochloride, Aminolevulinic Acid

    13. Levulan

    2.3.2 Depositor-Supplied Synonyms

    1. 5451-09-2

    2. Aminolevulinic Acid Hydrochloride

    3. Levulan

    4. 5-amino-4-oxopentanoic Acid Hydrochloride

    5. Levulan Kerastick

    6. 5-aminolevulinic Acid Hcl

    7. Gliolan

    8. Aminolevulinic Acid Hcl

    9. Ameluz

    10. Delta-aminolevulinic Acid Hydrochloride

    11. Mfcd00012869

    12. Alaglio

    13. Gleolan

    14. Alabel

    15. Pentanoic Acid, 5-amino-4-oxo-, Hydrochloride

    16. 5-aminolevulinic Acid, Hcl

    17. 5-aminolevulinic Acid (hydrochloride)

    18. 5-aminolevulinate Hydrochloride

    19. 5-ala

    20. Nsc-18509

    21. V35kbm8jgr

    22. 5-aminolevulinic Acid Hydrochloride Salt

    23. .delta.-aminolevulinic Acid Hydrochloride

    24. 5-amino-4-oxopentanoic Acid;hydrochloride

    25. Npc-07

    26. (4-carboxy-2-oxobutyl)azanium;chloride

    27. 5-amino-4-oxopentanoic Acid Hcl

    28. Aminolevulinic Acid Hydrochloride [usan]

    29. Ncgc00095111-01

    30. Dsstox_cid_25914

    31. Dsstox_rid_81222

    32. Dsstox_gsid_45914

    33. 5-amino-4-oxopentanoic Acid Hydrochloride;5-amino-4-oxopentanoic Acid

    34. Cas-5451-09-2

    35. 5-amino-levulinic Acid Hydrochloride

    36. 5-aminolevulinic Acid Hydrochloride, >=97.0% (at)

    37. Alacare

    38. Ala Hydrochloride

    39. Einecs 226-679-5

    40. Gleolan (tn)

    41. Levulan (tn)

    42. Ameluz (tn)

    43. Nsc 18509

    44. Ala Hcl

    45. Ala-pdt

    46. Levulinic Acid, 5-amino-, Hydrochloride

    47. Unii-v35kbm8jgr

    48. 5-amino-3-oxopentanoic Acid (hydrochloride)

    49. 5-aminolevulinic Acid.hcl

    50. Ala;5-ala

    51. Pentanoic Acid, Hydrochloride

    52. 5-amino-4-keto-valeric Acid

    53. Schembl192308

    54. Spectrum1504184

    55. Chembl1200582

    56. Dtxsid5045914

    57. Chebi:132969

    58. Hms1922f13

    59. Pd-p-506-a

    60. Pharmakon1600-01504184

    61. 5 Ala Hcl (trivial Name)

    62. Act05562

    63. Bcp02161

    64. Hy-n0305

    65. Nsc18509

    66. 5-amino Levulinic Acid Hydrochloride

    67. Tox21_111426

    68. Ccg-39079

    69. Nsc758687

    70. Akos015904495

    71. Aminolevulinic Acid Hcl [inci]

    72. Tox21_111426_1

    73. Ac-4252

    74. Bcp9000174

    75. Gs-3020

    76. Nsc-758687

    77. 4-carboxy-2-oxobutan-1-aminium Chloride

    78. 5-aminolevulinic Acid Hydrochloride, Gmp

    79. Ncgc00095111-02

    80. Ncgc00095111-03

    81. Ncgc00178086-03

    82. 5451-09-2 (hcl)

    83. Sy017972

    84. Db-005367

    85. 5-aminolevulinic Acid Hydrochloride, >=98%

    86. A0325

    87. Am20100341

    88. S2553

    89. Sw218068-2

    90. Aminolevulinic Acid Hydrochloride (jan/usan)

    91. A-6100

    92. A-6102

    93. A-6103

    94. A-6105

    95. Aminolevulinic Acid Hydrochloride [jan]

    96. D02908

    97. Aminolevulinic Acid Hydrochloride [mart.]

    98. 451a092

    99. Aminolevulinic Acid Hydrochloride [usp-rs]

    100. Aminolevulinic Acid Hydrochloride [who-dd]

    101. .delta.-aminolevulinic Acid Hydrochloride [mi]

    102. 5-aminolevulinic Acid Hydrochloride [ema Epar]

    103. Aminolevulinic Acid Hydrochloride [orange Book]

    104. Q27291473

    105. Aminolevulinic Acid Hydrochloride [usp Monograph]

    106. 0c1e43db-1221-4963-bfa4-18d3170000a4

    107. 5-aminolevulinic Acid Hydrochloride, Particle Size < 0.25 Mm

    108. Aminolevulinic Acid Hydrochloride Component Of Sonala001

    109. Aminolevulinic Acid Hydrochloride Component Of Sonala-001

    110. 5-aminolevulinic Acid Hydrochloride, Bioreagent, Suitable For Cell Culture, Powder, >=98%

    111. Aminolevulinic Acid Hcl; Aminolevulinic Acid Hydrochloride;ala; 5-ala;aminolevulinic Acid

    112. Aminolevulinic Acid Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-07-19
    3 Chemical and Physical Properties
    Molecular Weight 167.59 g/mol
    Molecular Formula C5H10ClNO3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count4
    Exact Mass167.0349209 g/mol
    Monoisotopic Mass167.0349209 g/mol
    Topological Polar Surface Area80.4 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity121
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameLevulan
    PubMed HealthAminolevulinic Acid (On the skin)
    Drug ClassesPhotosensitizing Agent
    Active IngredientAminolevulinic acid hydrochloride
    Dosage FormSolution
    RouteTopical
    Strength20%
    Market StatusPrescription
    CompanyDusa

    2 of 2  
    Drug NameLevulan
    PubMed HealthAminolevulinic Acid (On the skin)
    Drug ClassesPhotosensitizing Agent
    Active IngredientAminolevulinic acid hydrochloride
    Dosage FormSolution
    RouteTopical
    Strength20%
    Market StatusPrescription
    CompanyDusa

    4.2 Drug Indication

    Treatment of actinic keratosis of mild to moderate severity on the face and scalp (Olsen grade 1 to 2; see section 5. 1) and of field cancer ization in adults.

    Treatment of superficial and/or nodular basal cell carcinoma unsuitable for surgical treatment due to possible treatment-related morbidity and/or poor cosmetic outcome in adults.

    Gliolan is indicated in adult patients for visualisation of malignant tissue during surgery for malignant glioma (World Health Organization grade III and IV).

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Photosensitizing Agents

    Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms. (See all compounds classified as Photosensitizing Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Optical Imaging Agent [EPC]; Porphyrin Precursor [EPC]; Porphyrinogens [CS]; Fluorescence Contrast Activity [MoA]; Porphyrin Precursor [EPC]
    5.3 ATC Code

    L01XD04

    L01XD04